Boron tribromide → Allyl 3-{1-[4-(allyloxycarbonyl)-4-methylcyclohexyl]methoxy}-4-hydroxycinnamate

HRID 2225503노트

반응식

HRID 2225503 반응식
B(Br)(Br)Br.[CH2:5]([O:8][C:9]([C:11]1([CH3:35])[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=2[O:33]C)[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH2:13][CH2:12]1)=[O:10])[CH:6]=[CH2:7].[Cl-].[NH4+]>C(Cl)Cl>[CH2:5]([O:8][C:9]([C:11]1([CH3:35])[CH2:12][CH2:13][CH:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=2[OH:33])[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH2:15][CH2:16]1)=[O:10])[CH:6]=[CH2:7]

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 53660565Allyl 3-[1-(4-allyloxycarbonyl-4-methylcyclohexyl)methoxy]-4-methoxycinnamate

생성물 1

HCID 54284301Allyl 3-{1-[4-(allyloxycarbonyl)-4-methylcyclohexyl]methoxy}-4-hydroxycinnamate수율 38.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

At -78° C., 0.3 ml of boron tribromide was added to a solution of 0.7 g of allyl 3-[1-(4-allyloxycarbonyl-4-methylcyclohexyl)methoxy]-4-methoxycinnamate (Example 47) in 10 ml of methylene chloride. The solution was reacted for 20 minutes in this state. After reaction, 20 ml of an aqueous ammonium chloride solution was added to the reaction solution. The solution was extracted three times with 30 ml of ethyl acetate. The oily substance obtained was washed three times with an aqueous sodium chloride solution and was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo, yielding 0.26 g of allyl 3-{1-[4-(allyloxycarbonyl)-4-methylcyclohexyl]methoxy}-4-hydroxycinnamate (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

후처리

  1. customThe solution was reacted for 20 minutes in this state
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted three times with 30 ml of ethyl acetate
  4. customThe oily substance obtained
  5. washwas washed three times with an aqueous sodium chloride solution
  6. dry with materialwas dried over magnesium sulfate
  7. customThereafter, the solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-33153a5c13c343b7951a29e5f4c4c222
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05344845

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