Water → HCID 15125135, compound

HRID 373380Notes

Reaction equation

HRID 373380 reaction equation
[C:1]([C:4]1[C:5]([CH3:32])=[C:6]([C:14]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)(O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[C:7]([O:12]C)=[C:8]([CH3:11])[C:9]=1[CH3:10])(=[O:3])[CH3:2].B(Br)(Br)Br.O>ClCCl>[C:1]([C:4]1[C:5]([CH3:32])=[C:6]([CH:14]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:7]([OH:12])=[C:8]([CH3:11])[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 19812448HCID 19812448, compound

Product 1

HCID 15125135HCID 15125135, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 7-(3-acetyl-6-methoxy-2,4,5-trimethylphenyl)-7-(4-fluorophenyl)-7-hydroxyheptanoate (1.6 g) in dichloromethane (15 ml) was added dropwise to a solution of boron tribromide (1.4 ml) in dichloromethane (15 ml) at -78° C. The temperature was raised slowly to room temperature and the mixture was stirred for 5 hours. The reaction mixture was ice-cooled and water was added. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to obtain 7-(3-acetyl-6-hydroxy-2,4,5-trimethylphenyl)-7-(4-fluorophenyl)heptanoic acid (0.87 g) (Compound 35). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. temperaturecooled
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-64c05ec785484d19956f4ee102319459
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

Loading…