Triethylamine → 1-O-benzyl-3-O-t-butyldimethylsilylglycerol

HRID 1636284Notes

Reaction equation

HRID 1636284 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][OH:13])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)Cl>[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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 980723-(Benzyloxy)-1,2-propanediol

Product 1

HCID 156217871-O-benzyl-3-O-t-butyldimethylsilylglycerolYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-O-monobenzyl glycerol (1.58 g) in methylene chloride (20 ml), t-butyldimethylsilyl chloride (1.44 g) and then triethylamine (1.33 ml) and N,N-dimethylaminopyridine (0.04 g) were added, and the mixture was stirred overnight at room temperature. Methylene chloride (20 ml) was further added to the reaction liquid, and the mixture was washed with water (20 ml×3) and saturated ammonium chloride (20 ml×3), dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain pale yellow oil. The product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=7/1) to obtain the desired product (1.93 g) as pale yellow liquid.

Workup

  1. washthe mixture was washed with water (20 ml×3) and saturated ammonium chloride (20 ml×3)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customto obtain pale yellow oil
  5. customThe product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-f624a6d707ed4c74a8dfdef89755c6b1
Source dataset
uspto-grants-2000_03
Patent number
US06034087

Reaction notes

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