Boron tribromide → (2RS,3SR)-2-acetoxy-3-(3-hydroxy-4-phenoxyphenyl)-5-phenylpentane

HRID 849370Notes

Reaction equation

HRID 849370 reaction equation
[C:1]([O:4][CH:5]([CH:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:18]([O:29]CC2C=CC=CC=2)[CH:17]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:6])(=[O:3])[CH3:2].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:1]([O:4][CH:5]([CH:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:18]([OH:29])[CH:17]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 19591477(2RS,3SR)-2-acetoxy-3-(3-benzyloxy-4-phenoxyphenyl)-5-phenylpentane

Product 1

HCID 19591491(2RS,3SR)-2-acetoxy-3-(3-hydroxy-4-phenoxyphenyl)-5-phenylpentaneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

200 mg of (2RS,3SR)-2-acetoxy-3-(3-benzyloxy-4-phenoxyphenyl)-5-phenylpentane was dissolved in 5 ml of methylene chloride, and 0.2 ml of boron tribromide was added under cooling to -78° C., followed by stirring at the same temperature for 3 hours. Then, the temperature was gradually brought to 0° C. The reaction solution was poured into a saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate and then washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1), to obtain 161 mg (yield: 85%) of the above identified compound as a colorless oily substance.

Workup

  1. customwas gradually brought to 0° C
  2. extractionextracted with ethyl acetate
  3. washwashed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1)
  8. customto obtain 161 mg (yield: 85%) of the

Sources & evidence

ORD record
ord-09fa59a197f94e6aa9120642099adfe1
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

Loading…