Dimethyl Sulfoxide → 3-o-t-Butyldimethylsilyl-2-o-methyl-rac-glyceraldehyde

HRID 497006Notes

Reaction equation

HRID 497006 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][CH2:19][CH:20]([CH2:23][OH:24])[O:21][CH3:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[Si:11]([O:18][CH2:19][CH:20]([O:21][CH3:22])[CH:23]=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 223164511-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

Product 1

HCID 543075043-o-t-Butyldimethylsilyl-2-o-methyl-rac-glyceraldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oleyl 2-O-methyl-rac-glycerate (Compound 76) To a solution of oxalyl chloride (87 (L, 1.0 mmol) in CH2Cl2 (7 mL) at −78° C. was added DMSO (71 (L, 1.0 mmol). After 20 min, alcohol Compound 42 (0.20 g, 0.91 mmol) was added followed, after another 20 min, by the addition of triethylamine (0.63 mL, 4.6 mmol). The reaction was warmed to room temperature over a 10 min period, filtered through a plug of silica-gel, which was washed with ethyl acetate (50 mL) and concentrated to give 3-O-t-butyldimethylsilyl-2-O-methyl-rac-glyceraldehyde Compound 73 (0.20 g, 100%) as a colourless oil.

Workup

  1. filtrationfiltered through a plug of silica-gel, which
  2. washwas washed with ethyl acetate (50 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7e2d0504d2a146d8ae2b7e08bfca9af3
Source dataset
uspto-grants-2005_09
Patent number
US06949528B1

Reaction notes

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