Potassium Carbonate → HCID 86760619, 화합물

HRID 2057331노트

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HRID 2057331 반응식
[CH2:1]([O:8][C:9](=[O:20])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([CH:18]=O)[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(CC)C>[CH2:1]([O:8][C:9](=[O:20])[N:10]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[CH:26][CH2:25][CH2:24][CH2:23][Br:22])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2733851(4-Bromobutyl)triphenylphosphanium bromideHCID 178485996HCID 178485996, 화합물

생성물 1

HCID 86760619HCID 86760619, 화합물

시약·촉매·용매 1

HCID 64052-Methyl-2-butanol용매

실험 절차

A solution of 126.5 g (459.4 mmol) of trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester in 1.27 l 2-methyl-2-butanol was treated with 263.6 g (551.3 mmol) (4-bromobutyl)triphenylphosphonium bromide and 254 g (1838 mmol) of K2CO3 and was heated at reflux for 3.5 h. The reaction was cooled (RT), filtered and evaporated. The residue was suspended in hexane (1.8 l, first at RT then at 0° C.) and filtered. Purification by column chromatography on silica gel (hexane/EtOAc 4:1) gave 149.9 g (83%) of trans-(1 E/Z)-[4-(5-Bromo-pent-1-enyl)-cyclohexyl]-methyl-carbamic acid benzyl ester, MS: 293 (M, 1Br).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 h
  3. filtrationfiltered
  4. customevaporated
  5. filtrationfirst at RT then at 0° C.) and filtered
  6. customPurification by column chromatography on silica gel (hexane/EtOAc 4:1)

출처 및 근거

ORD 기록
ord-4005ec2e19c74c5c82a97a7853be0a42
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335687B2

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