Benzyl Bromide → HCID 69943797, compound

HRID 1978089Notes

Reaction equation

HRID 1978089 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:12][C:13]([C@H:15]([CH2:22][CH:23]([CH3:25])[CH3:24])[C@H:16]([OH:21])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[CH:10]=[CH2:11].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)C.[Ag-]=O>[CH2:9]([O:12][C:13]([C@H:15]([CH2:22][CH:23]([CH3:25])[CH3:24])[C@H:16]([O:21][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:17]([O:19][CH3:20])=[O:18])=[O:14])[CH:10]=[CH2:11]

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 86756754HCID 86756754, compound

Product 1

HCID 69943797HCID 69943797, compound

Reagents, catalysts & solvents 3

HCID 178418778HCID 178418778, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

0.51 g of silver(I) oxide and 0.33 ml of benzyl bromide were added to a solution of 0.27 g of methyl 3(R)-(allyloxycarbonyl)-2(S)-hydroxy-5-methylhexanoate in 5 ml of dimethylformamide. After stirring the mixture for 24 hours, 0.36 g of cesium carbonate were added and stirring was continued for 3 hours. The mixture was diluted with diethyl ether and filtered. The filtrate was then washed in succession with 5% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate, water and brine. The diethyl ether phase was dried over anhydrous magnesium sulphate and the solvent was evaporated. The residue was purified by flash column chromatography on silica gel using ethyl acetate/hexane (1:19) for the elution. There was obtained 0.16 g of methyl 3(R)-(allyloxycarbonyl)-2(S)-benzyloxy-5-methylhexanoate in the form of a clear oil.

Workup

  1. stirringstirring
  2. waitwas continued for 3 hours
  3. filtrationfiltered
  4. washThe filtrate was then washed in succession with 5% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate, water and brine
  5. dry with materialThe diethyl ether phase was dried over anhydrous magnesium sulphate
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-d5277386a4f14f62ab24290c9c8bfd5e
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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