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

HRID 2298790Notes

Reaction equation

HRID 2298790 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+].[CH2:23]1COCC1>>[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

4

Reactant 3

HCID 8028TetrahydrofuranHCID 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%

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, Mel (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. additionMel (10 mL, 0.17 mol) was added and, after another 3 hours
  2. customthe mixture was quenched with H2O (150 mL)
  3. extractionextracted into diethyl ether (500 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification of the residue by silica-gel column chromatography [eluent: hexane/ethyl acetate, 90/10, v/v]

Sources & evidence

ORD record
ord-c6c63d5db498412589ab78b46ba1896a
Source dataset
uspto-grants-2002_12
Patent number
US06495532B1

Reaction notes

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