Benzyl Bromide → HCID 69943797、化合物

HRID 1978089ノート

反応式

HRID 1978089 の反応式
[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]

参加物

7

反応物 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 86756754HCID 86756754、化合物

生成物 1

HCID 69943797HCID 69943797、化合物

試薬・触媒・溶媒 3

HCID 178418778HCID 178418778、化合物触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5277386a4f14f62ab24290c9c8bfd5e
出典データセット
uspto-grants-2001_05
特許番号
US06235787B1

反応ノート

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