Water → HCID 11143440, compound

HRID 862213Notes

Reaction equation

HRID 862213 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].[C:24]1(C)C=CC(S(OC)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.C(OCC)(=O)C>[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

7

Reactant 4

HCID 962WaterHCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 10451669HCID 10451669, compound

Product 1

HCID 11143440HCID 11143440, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2.58 g (7.0 mmol.) of (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoic acid was dissolved in 16 ml of acetone. To the acetone solution were added 6.52 g (35 mmol.) of methyl p-toluenesulfonate and 1.06 g (7.7 mmol.) of potassium carbonate, and the resulting mixture was vigorously stirred for 6 hours at room temperature to give a reaction solution. The reaction solution was mixed with 16 ml of water and then extracted with 20 ml of toluene. The toluene portion was dried over anhydrous magnesium sulfate and concentrated to give an oil. The oil was treated by column chromatography (eluent: ethyl acetate) to give 1.91 g (5.0 mmol.) of methyl (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoate as an oil (yield: 71%).

Workup

  1. customto give a reaction solution
  2. extractionextracted with 20 ml of toluene
  3. dry with materialThe toluene portion was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil

Sources & evidence

ORD record
ord-5ca7102e85a442c58bd7a52cf8c6211a
Source dataset
uspto-grants-1998_02
Patent number
US05717124

Reaction notes

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