tert-Butyl acetate → tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

HRID 1071156Notes

Reaction equation

HRID 1071156 reaction equation
[H-].[Na+].[Cl-].[Mg+2].[Cl-].[C:6]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH3:7].[Cl:14][CH2:15][C@@H:16]([OH:23])[CH2:17][C:18](OCC)=[O:19].C([N-]C(C)C)(C)C.[Li+]>CCCCCC.O1CCCC1>[Cl:14][CH2:15][C@@H:16]([OH:23])[CH2:17][C:18](=[O:19])[CH2:7][C:6]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

8

Reactant 5

HCID 10908tert-Butyl acetateHCID 24758Sodium hydrideHCID 2724682Lithium diisopropylamideHCID 5360315Magnesium ChlorideHCID 7019277Ethyl (3S)-4-chloro-3-hydroxybutanoate

Product 1

HCID 7022053tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Separately, 240 mg (6 mmol equivalent) of sodium hydride (60% in mineral oil) was washed with hexane and, then, 6 ml of tetrahydrofuran was added. Then, at 5° C., 1.71 g (18.0 mmol) of magnesium chloride, 1.74 g (15.0 mmol) of tert-butyl acetate and 1.0 g (6 mmol) of ethyl (3S)-4-chloro-3-hydroxybutyrate were added and the mixture was stirred for 30 minutes. To this mixture, the lithium diisopropylamide solution prepared above was added dropwise over 10 minutes at the same temperature and the reaction mixture was further stirred at an elevated temperature of 25° C. for 3 hours.

Workup

  1. additionabove was added dropwise over 10 minutes at the same temperature
  2. stirringthe reaction mixture was further stirred at an elevated temperature of 25° C. for 3 hours

Sources & evidence

ORD record
ord-5b221e68cf104c3e8b3b527fb1de89d6
Source dataset
uspto-grants-2005_06
Patent number
US06903225B2

Reaction notes

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