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Potassium Carbonate → 1,2-dibenzyl 1-tert.butyl 4-methyl-1-(5-phenyl-pent-2-en-1-yl)-1,1,2(R)-pentanetricarboxylate

HRID 1464363
ノート
印刷プレビュー

反応式

HRID 1464363 の反応式
[CH:1]([CH2:3][C:4]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@H:5]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:6][CH:7]([CH3:9])[CH3:8])=O.C(=O)([O-])[O-].[K+].[K+].[Br-].[C:44]1([CH2:50][CH2:51][CH2:52][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCCC1>[CH3:9][CH:7]([CH3:8])[CH2:6][C@@H:5]([C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])[C:4]([CH2:3][CH:1]=[CH:52][CH2:51][CH2:50][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 109286473-Phenylpropyl triphenylphosphonium bromideHCID 867477791,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

生成物 1

HCID 678264681,2-dibenzyl 1-tert.butyl 4-methyl-1-(5-phenyl-pent-2-en-1-yl)-1,1,2(R)-pentanetricarboxylate収率 66.4%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

A mixture of 0.496 g of 1,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentane tricarboxylate, 0.176 g of potassium carbonate and 0.576 g of 3-phenylpropyltriphenylphosphonium bromide in 8 ml of dry tetrahydrofuran was heated at reflux under a nitrogen atmosphere for 3 days. The solvent was removed by evaporation and stirred with diethyl acetate. The solids which separated were filtered off and the filtrate was evaporated. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (6:1) for the elution. There was obtained 0.397 g of 1,2-dibenzyl 1-tert.butyl 4-methyl-1-(5-phenyl-pent-2-en-1-yl)-1,1,2(R)-pentanetricarboxylate in the form of a colorless oil.

後処理

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 3 days
  3. customThe solvent was removed by evaporation
  4. customThe solids which separated
  5. filtrationwere filtered off
  6. customthe filtrate was evaporated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washfor the elution

出典と根拠

ORDレコード
ord-5c9379443acd4f52a3f6cb16c13df896
出典データセット
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05304549

反応ノート

読み込み中…

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