Triethylamine → 5-(tert-Butyl-dimethyl-silyloxy)-4-hydroxy-pentanoic Acid Ethyl Ester

HRID 8187Notes

Reaction equation

HRID 8187 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH2:6][CH:7]([OH:10])[CH2:8][OH:9])[CH3:2].[C:12]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH2:6][CH:7]([OH:10])[CH2:8][O:9][Si:16]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:18])[CH3:17])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 570939564,5-Dihydroxy-pentanoic Acid Ethyl Ester

Product 1

HCID 865926205-(tert-Butyl-dimethyl-silyloxy)-4-hydroxy-pentanoic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4,5-dihydroxy-pentanoic acid ethyl ester, (7 g, 43.2 mmol) and 4-dimethylaminopyridine (0.2 g, 1.73 mmol) in dichloromethane (145 mL) at room temperature under nitrogen is treated with tert-butyl-dimethyl-silyl chloride (7.8 g, 51.85 mmol) and triethylamine (6.9 mL, 47.52 mmol) and stirred 18 h. The mixture is diluted with dichloromethane (100 mL), washed with water (100 mL), saturated ammonium chloride solution, and brine. The solution is filtered and concentrated in vacuo to yield the title compound, 11.85 g (99%), as a colorless oil.

Workup

  1. washwashed with water (100 mL), saturated ammonium chloride solution, and brine
  2. filtrationThe solution is filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7d7674ad59d4f66821709f6ec79f701
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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