Water → HCID 54532647, compound

HRID 862215Notes

Reaction equation

HRID 862215 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].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:12])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10451669HCID 10451669, compound

Product 1

HCID 54532647HCID 54532647, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.84 g (4.99 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 2.56 g (15.0 mmol.) of benzyl bromide and 0.76 g (5.5 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 12 ml of water and then extracted with 12 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 1.99 g (4.34 mmol.) of benzyl (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoate (optical purity: 99% ee) as an oil (yield: 87%).

Workup

  1. customto give a reaction solution
  2. extractionextracted with 12 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-93db0e5adbd84310b2a98ffd759cf621
Source dataset
uspto-grants-1998_02
Patent number
US05717124

Reaction notes

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