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

HRID 993419Notes

Reaction equation

HRID 993419 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-a5b5c6ba3bcc418cb3707e40ce80c592
Source dataset
uspto-grants-2002_10
Patent number
US06472544B1

Reaction notes

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