Diisopropyl Ether → Methyl 3-(3-bromo-4-cyclopentyloxyphenyl)propionate

HRID 2378527Notes

Reaction equation

HRID 2378527 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[H-].[Na+].Br[CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(OC(C)C)(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 22558720Methyl 3-(3-bromo-4-hydroxyphenyl)propanoate

Product 1

HCID 22559058Methyl 3-(3-bromo-4-cyclopentyloxyphenyl)propionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of Intermediate 5 (4.50 g) in DMF (20 ml) was added with 60% sodium hydride (440 mg, KANTO) under ice cooling. The reaction mixture was stirred for 10 minutes, then added with bromocyclopentane (1.61 ml, TCI), warmed to room temperature, stirred for 1.5 hours, then warmed to 60° C., and further stirred for 16 hours. The reaction mixture was added with water (50 ml) and isopropyl ether (300 ml)) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:isopropyl ether=7:1) to obtain the title compound (Compound No. A-5, 2.50 g).

Workup

  1. stirringstirred for 1.5 hours
  2. temperaturewarmed to 60° C.
  3. stirringfurther stirred for 16 hours
  4. extractionfor extraction
  5. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography (hexane:isopropyl ether=7:1)

Sources & evidence

ORD record
ord-d64cb93198f94056b0ef1b00ca6c4345
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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