ChemicalBook CAS DataBase List methoxymethanol

methoxymethanol synthesis

11synthesis methods

Product Name:methoxymethanol
CAS Number:4461-52-3
Molecular formula:C2H6O2
Molecular Weight:62.07

4009-98-7 Synthesis

(Methoxymethyl)triphenylphosphonium chloride

4009-98-7
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$5.00/10g

165047-24-5 Synthesis

165047-24-5
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$6.00/1g

4461-52-3
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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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Yield:-

Reaction Conditions:

Stage #1:(methoxymethyl)triphenylphosphonium chloride with potassium tert-butylate in tetrahydrofuran at 20; for 1 h;
Stage #2:2,4,5-trifluorobenzaldehyde in tetrahydrofuran at 20; for 48 h;optical yield given as %de;Wittig reaction;

Steps:

tert-Butyl (E)-4-(2',4',5'-trifluorophenyl)but-2-enoate 6
Step 1: KO^tBu (17.5 g, 156.3 mmol) was added to methoxymethyltriphenylphosphonium chloride (53.6 g, 156 mmol) in THF (300 mL) at rt and the resultant mixture was stirred for 1 h. 2,4,5-Triflurobenzaldehyde 4 (5.0 g, 31.3 mmol) was added dropwise at rt and stirring was continued at rt for 48 h. The suspension was filtered and the filter cake was washed with EtOAc (3 45 mL). The combined organics were sequentially washed with satd aq NH₄Cl (500 mL), brine (300 mL), then dried and concentrated in vacuo. Purification via flash column chromatography (eluent hexane/EtOAc, 20:1) gave a 1:1 mixture of 5 (55:45 dr) and a by-product (which was tentatively assigned as methoxymethanol) as a light yellow oil (7.19 g). Data for (E)-5: δ_H(400 MHz, CDCl₃) 3.72 (3H, s, OMe), 5.80 (1H, d, J 13.0, HC=CH), 6.926.96 (1H, m, Ar), 7.027.08 (1H, m, Ar), 7.15 (1H, d, J 13.0, HC=CH). Data for (Z)-5: δ_H(400 MHz, CDCl₃) 3.82 (3H, s, OMe), 5.44 (1H, d, J 7.0, HC=CH), 6.26 (1H, d, J 7.0, HC=CH), 7.027.08 (1H, m, Ar), 7.747.79 (1H, m, Ar). Data for methoxymethanol:^² δ_H(400 MHz, CDCl₃) 3.41 (3H, s, OMe), 4.46 (2H, s, CH₂).

References:

Davies, Stephen G.;Fletcher, Ai M.;Lv, Linlu;Roberts, Paul M.;Thomson, James E. [Tetrahedron Letters,2012,vol. 53,# 24,p. 3052 - 3055] Location in patent:supporting information; experimental part

67-56-1 Synthesis