Boron tribromide → HCID 53667928, compound

HRID 2225504Notes

Reaction equation

HRID 2225504 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:18]=[CH:17][C:10]([CH:11]=[CH:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][C:8]=1[O:19][CH2:20][C:21]12[CH2:28][CH2:27][C:24]([CH3:29])([CH2:25][CH2:26]1)[O:23][C:22]2=[O:30].[Cl-].[NH4+]>C(Cl)Cl>[OH:6][C:7]1[CH:18]=[CH:17][C:10]([CH:11]=[CH:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][C:8]=1[O:19][CH2:20][C:21]12[CH2:28][CH2:27][C:24]([CH3:29])([CH2:25][CH2:26]1)[O:23][C:22]2=[O:30]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 54420208HCID 54420208, compound

Product 1

HCID 53667928HCID 53667928, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At -78° C., 0.3 ml of boron tribromide was added to a solution of 0.68 g of methyl 4-methoxy-3-[1-(4-methyl-2-oxo-3-oxabicyclo[2.2.2]octanyl)methoxy]cinnamate (Example 50) in 10 ml of methylene chloride. The solution was reacted for 15 minutes, as it was. After reaction, 30 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 organic layer 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 0.21 g of methyl 4-hydroxy-3-[1-(4-methyl-2-oxo-3-oxabicyclo[2.2.2]octanyl)methoxy]cinnamate (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 15 minutes, as it
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted three times with 30 ml of ethyl acetate
  4. customThe organic layer 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-4d4e7c0a8aab423d87416642857b16fc
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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