Acetone → HCID 54467078, compound

HRID 862212Notes

Reaction equation

HRID 862212 reaction equation
[Si:1]([O:8][C@H:9]([CH2:14][C:15](=[O:31])[CH2:16][P:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18])[CH2:10][C:11]([OH:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CI.[C:34](=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[Si:1]([O:8][C@H:9]([CH2:14][C:15](=[O:31])[CH2:16][P:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18])[CH2:10][C:11]([O:13][CH3:34])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 54027781HCID 54027781, compound

Product 1

HCID 54467078HCID 54467078, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.92 g (2 mmol.) of (R)-3-t-butyldimethylsilyloxy-6-diphenylphosphinoyl-5-oxohexanoic acid prepared above, 0.28 g of methyl iodide, 0.28 g of potassium carbonate and 10 ml of acetone were added, and then the mixture was stirred for 8 hours at room temperature. After 16 ml of water was added to the solution, the solution was extracted with two portions of 20 ml of ethyl acetate. The ethyl acetate portions were combined and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation in vacuo to give 0.81 g of methyl (R)-3-t-butyldimethylsilyloxy-6-diphenylphosphinoyl-5-oxohexanoate as a colorless oil (optical purity: 98% ee; yield: 85% based on the amount of (R)-3-t-butyldimethylsilyloxy-6-diphenylphosphinoyl-5-oxohexanoic acid).

Workup

  1. additionwere added
  2. extractionthe solution was extracted with two portions of 20 ml of ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation in vacuo

Sources & evidence

ORD record
ord-0be021052aca43289757616fa36f7715
Source dataset
uspto-grants-1998_02
Patent number
US05717124

Reaction notes

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