Methyl iodide → 1-o-Benzyl-3-o-t-butyldimethylsilyl-2-o-methyl-rac-glycerol

HRID 496995Notes

Reaction equation

HRID 496995 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I>C1COCC1>[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[O:11][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 156217871-O-benzyl-3-O-t-butyldimethylsilylglycerol

Product 1

HCID 223164691-o-Benzyl-3-o-t-butyldimethylsilyl-2-o-methyl-rac-glycerolYield 74,475.703%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Alcohol Compound 40 (48.8 g, 0.16 mmol) was added to a mixture of NaH (4.0 g, 0.17 mol) in dry THF (500 mL). After 5 min, MeI (10 mL, 0.17 mol) was added and, after another 3 hours, the mixture was quenched with H2O (150 mL), extracted into diethyl ether (500 mL), dried (MgSO4) and concentrated. Purification of the residue by silica-gel column chromatography [eluent: hexane/ethyl acetate, 90/10, v/v] yielded 1-O-benzyl-3-O-t-butyldimethylsilyl-2-O-methyl-rac-glycerol (Compound 41) (37 g, 74%) as a yellow oil.

Workup

  1. customthe mixture was quenched with H2O (150 mL)
  2. extractionextracted into diethyl ether (500 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the residue by silica-gel column chromatography [eluent: hexane/ethyl acetate, 90/10, v/v]

Sources & evidence

ORD record
ord-06295222e994404b8e3c5a40da81dc26
Source dataset
uspto-grants-2005_09
Patent number
US06949529B2

Reaction notes

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