Cesium acetate → Tert-butyl [4-(acetoxymethyl)phenyl](cyclopentyl)acetate

HRID 877187Notes

Reaction equation

HRID 877187 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1.[C:22]([O-:25])(=[O:24])[CH3:23].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[C:22]([O:25][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 5152919Cesium acetateHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

Product 1

HCID 58136319Tert-butyl [4-(acetoxymethyl)phenyl](cyclopentyl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

20.0 g (75% pure, 42.5 mmol) of tert-butyl(+/−)-[4-(bromomethyl)phenyl](cyclopentyl)acetate were added to a suspension of 16.3 g (84.9 mmol) of cesium acetate in 80 ml of DMF. The resulting mixture was heated at 50° C. for 1.5 h. After cooling, the mixture was diluted with ethyl acetate, washed successively with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1→about 10:1). This gave 11.7 g (76.4% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. washwashed successively with water and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1→about 10:1)

Sources & evidence

ORD record
ord-f6593c26abf44078ae9a785cd9e68e67
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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