ChemicalBook CAS DataBase List N,N-Dimethylformamide di-tert-butyl acetal

N,N-Dimethylformamide di-tert-butyl acetal synthesis

5synthesis methods

Product Name:N,N-Dimethylformamide di-tert-butyl acetal
CAS Number:36805-97-7
Molecular formula:C11H25NO2
Molecular Weight:203.32

A mixture of 59.5 g (0.5 mol) of N, N-dimethylformamide dimethyl acetal and 147 mL (1.5 mol) of dry tert-butanol in a three-necked flask (250 mL) fitted with a thermometer magnetic stirrer, nitrogen inlet and a 33 x 1.9 cm silvered vacuum jacketed Goodloe column which was equipped with a reflux controlled take-off distilling head was heated at reflux for 1 hr, then 300 mg of 2,4,6-tri-tert-butylphenol was added. The reaction mixture was heated at 100-115°C for 48 hrs, during which time, at the rate of two drops/min, 56 mL of distillate was collected. Another 50 mL (0.52 mol) of tert-butanol was added to the reaction mixture, and the removal of methanol was continued for an additional 42 hrs to afford 64 mL of distillate. Distillation of the crude product with a similar but smaller column (20 x 1.4 cm) gave 53.2 g (52%) of N, N-Dimethylformamide di-tert-butyl acetal[1].

865-47-4 Synthesis

865-47-4
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$14.00/25g

[(dimethylamino)methylene]dimethylammonium methyl sulphate

2013-91-4
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5762-56-1
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5815-08-7 Synthesis

5815-08-7
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N,N-Dimethylformamide di-tert-butyl acetal

36805-97-7
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$29.00/1g

Yield:-

Reaction Conditions:

in tetrahydrofuran at 60; for 1 h;

Steps:

14.1
Example 14: Tris(dimethylamino)methane (13, R6 = Me, R7 = Me), Tert-Butoxy- bis(dimethylamino)methane (14, R6 = Me, R7 = Me, R8 = tBu) and N,N- Dimethylformamide di-tert-butyl acetal (15, R6 = Me, R7 = Me, R8 = tBu); Method 1; N,N,N',N'-tetramethylformadinium methyl sufate (5 g) (prepared according to Example 1, X = MeSO₄) is added to a solution of potassium tert-butoxide in THF (23.6 ml, 1 M). The mixture is then stirred for 1 h at 60 °C. The reaction mixture is then filtered under argon. The mother liquor is then concentrated in vacuo to afford a residue (1.60 g) containing 13, 14 and 15 (R6 = Me, R7 = Me, R8 = tBu). 1H NMR (C₆D₆): 1.08, 1.16, 1.24, 2.29, 2.33, 3.02, 4.06, 5.00. Relative amounts of 13 (R6 = Me; R7 = Me), 14 (R6 = Me, R7 = Me, R8 = tBu), 15 (R6 = Me, R7 = Me, R8 = Me) are determined by integration of signals at 3.02, 4.06 and 5.00 ppm, respectively.

References:

NOVARTIS AG WO2009/90251, 2009, A2 Location in patent:Page/Page column 143-144

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865-47-4 Synthesis

865-47-4
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3218-35-7 Synthesis