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

HRID 2225503Notes

Reaction equation

HRID 2225503 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-33153a5c13c343b7951a29e5f4c4c222
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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