Benzyl Bromide → HCID 69943797, 화합물

HRID 1978089노트

반응식

HRID 1978089 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 69943797HCID 69943797, 화합물

시약·촉매·용매 3

HCID 178418778HCID 178418778, 화합물촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d5277386a4f14f62ab24290c9c8bfd5e
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235787B1

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