Acetone → HCID 11143440, compound

HRID 862216Notes

Reaction equation

HRID 862216 reaction equation
[Si:1]([O:8][C@H:9]([CH2:14][C:15](=[O:23])[CH2:16][P:17]([O:21][CH3:22])([O:19][CH3:20])=[O:18])[CH2:10][C:11]([OH:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:24]C(C)=O.CI.C(=O)([O-])[O-].[K+].[K+]>O>[Si:1]([O:8][C@H:9]([CH2:14][C:15](=[O:23])[CH2:16][P:17]([O:19][CH3:20])([O:21][CH3:22])=[O:18])[CH2:10][C:11]([O:13][CH3:24])=[O:12])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10451669HCID 10451669, compound

Product 1

HCID 11143440HCID 11143440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The concentrated solution (1.88 g) containing (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoic acid, which was prepared by concentrating the ethyl acetate portion, was obtained in the same manner as Example 1. To the solution, 24 ml of acetone were added to prepare an acetone solution. 3.1 g of methyl iodide and 0.60 g of potassium carbonate were added to the solution with stirring, and then the mixture was further stirred for 5 hours at room temperature. After 24 ml of water was added to the solution, the solution was extracted with two portios of 30 ml of ethyl acetate. The ethyl acetate portions were combined and dried over anhydrous magnesium sulfate. Then, the solvent was removed by distillation in vacuo to give 1.2 g of methyl (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoate as an oil (optical purity: 98% ee; purity: 79%).

Workup

  1. customwas prepared
  2. concentrationby concentrating the ethyl acetate portion
  3. customwas obtained in the same manner as Example 1
  4. stirringthe mixture was further stirred for 5 hours at room temperature
  5. extractionthe solution was extracted with two portios of 30 ml of ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThen, the solvent was removed by distillation in vacuo

Sources & evidence

ORD record
ord-d75b41acbb044c288fef9fcb44ca3925
Source dataset
uspto-grants-1998_02
Patent number
US05717124

Reaction notes

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