Water → HCID 11143440, compound

HRID 862214Notes

Reaction equation

HRID 862214 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 74%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.84 g (5.0 mmol.) of (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoic acid was dissolved in 11.5 ml of acetone. To the acetone solution were added 0.94 g (5.0 mmol.) of methyl p-toluenesulfonate and 0.76 g (5.5 mmol.) of potassium carbonate, and the resulting mixture was vigorously stirred for 14 hours at room temperature to give a reaction solution. The reaction solution was mixed with 12 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 1.41 g (3.7 mmol.) of methyl (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoate as an oil (yield: 74%).

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-7a8368d0b7044ca28862dac435af4719
Source dataset
uspto-grants-1998_02
Patent number
US05717124

Reaction notes

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