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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
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HRID 1464363 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c9379443acd4f52a3f6cb16c13df896
출처 데이터셋
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05304549

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