Allyl bromide → HCID 86756754, compound

HRID 1978088Notes

Reaction equation

HRID 1978088 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[C:5]([C@H:8]([CH2:15][CH:16]([CH3:18])[CH3:17])[C@H:9]([OH:14])[C:10]([O:12][CH3:13])=[O:11])([OH:7])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:7][C:5]([C@H:8]([CH2:15][CH:16]([CH3:18])[CH3:17])[C@H:9]([OH:14])[C:10]([O:12][CH3:13])=[O:11])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 22880382HCID 22880382, compound

Product 1

HCID 86756754HCID 86756754, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 ml of allyl bromide were added to a solution of 4.52 g of methyl 3(R)-carboxy-2(S)-hydroxy-5-methylhexanoate and 7.9 g of caesium carbonate in 30 ml of dimethylformamide. The mixture was stirred overnight and then evaporated. The residue was dissolved in dichloromethane and washed with 2M aqueous hydrochloric acid. The dichloromethane phase was then dried over anhydrous magnesium sulphate and the solvent was evaporated. The residue was purified by flash chromatography on silica gel using ethyl acetatelhexane (1:9 increasing to 2:8) for the elution. There were obtained 2.88 g of methyl 3(R)-(allyloxycarbonyl)-2(S)-hydroxy-5-methylhexanoate in the form of a pale yellow oil.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with 2M aqueous hydrochloric acid
  4. dry with materialThe dichloromethane phase was then dried over anhydrous magnesium sulphate
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-f99569cc78de461ebf5503244451ecc5
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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