ChemicalBook CAS DataBase List 3,4-dihydro-2H-1,4-benzoxazin-6-ol

3,4-dihydro-2H-1,4-benzoxazin-6-ol synthesis

9synthesis methods

Product Name:3,4-dihydro-2H-1,4-benzoxazin-6-ol
CAS Number:26021-57-8
Molecular formula:C8H9NO2
Molecular Weight:151.16

53412-38-7
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$65.00/100mg

26021-57-8
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$72.00/100mg

Yield:26021-57-8 100%

Reaction Conditions:

with borane-THF in tetrahydrofuran at 0 - 20;

Steps:

d
Compound 48 (0.39 g, 2.35 mmol) was dissolved in THF and IM BH₃-THF (7.05 ml, 7.05 mmol) was added to the reaction mixture at 0 ⁰C slowly over a time of 5 min. After the addition the reaction mixture was warmed to the room temperature and left overnight. Excess borane was destroyed by careful addition of methanol. The solvent was removed and the crude reaction mixture was extracted in EtOAc to give an oily pure compound in quantitative yield (0.34 g.). ¹H NMR(dmso-d₆): 8.48 (s, IH), 6.37 (d, IH, J=8.47 Hz), 5.96 (d, IH, J=2.75 Hz), 5.82 (dd, IH, J=8.44, 2.76 Hz), 3.97 (t, 2H, J=4.38 Hz), 3.18 (t, 2H, J=4.31 Hz). ¹³C NMR (dmso-d6): 152.2, 136.6, 135.8, 116.7, 103.8, 102.0, 65.0, 47.2. ES- HRMS [M+H]⁺ 152.0711. Calcd for (C₈Hi₀NO₂): 152.0711

References:

UNIVERSITY OF MASSACHUSETTS WO2009/36351, 2009, A2 Location in patent:Page/Page column 21; 22/24

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