Ethyl Acetate → 1-[3-(Cyclopentyloxy)-4-methoxyphenyl]butane-1,3-dione

HRID 2373187Notes

Reaction equation

HRID 2373187 reaction equation
[H-].[Na+].[C:3](OCC)(=[O:5])[CH3:4].[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([C:23](=[O:25])[CH3:24])[CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:13][CH2:12][CH2:11][CH2:10]1>O1CCCC1.C(O)C.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([C:23](=[O:25])[CH2:24][C:3](=[O:5])[CH3:4])[CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 117465791-(3-(Cyclopentyloxy)-4-methoxyphenyl)ethanone

Product 1

HCID 691556961-[3-(Cyclopentyloxy)-4-methoxyphenyl]butane-1,3-dioneYield 88.3%

Reagents, catalysts & solvents 3

HCID 702EthanolCatalystHCID 26541Dibenzo-18-crown-6CatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of 60% sodium hydride (200 mg, 5 mmol) and ethyl acetate (0.49 ml, 5 mmol) in tetrahydrofuran (25 ml) were sequentially added a solution of 1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethanone (European Patent Application EP470805) (590 mg, 2.5 mmol) in tetrahydrofuran (5 ml), two drops of ethanol and a solution of dibenzo-18-crown (15 mg, 0.04 mmol) in tetrahydrofuran (5 ml). The reaction mixture was refluxed for 5 h, allowed to cool to room temperature and finally quenched with aqueous 10% sulphuric acid solution (5 ml). The resulting mixture was diluted with diethyl ether, washed with saturated ammonium chloride solution, dried and concentrated under reduced pressure to yield a crude product which was purified by column chromatography (SiO2, hexane-ethyl acetate 4:1) to afford the title compound (610 mg, 86% yield) as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customfinally quenched with aqueous 10% sulphuric acid solution (5 ml)
  3. additionThe resulting mixture was diluted with diethyl ether
  4. washwashed with saturated ammonium chloride solution
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto yield a crude product which
  8. customwas purified by column chromatography (SiO2, hexane-ethyl acetate 4:1)

Sources & evidence

ORD record
ord-766344241a814ed3bcfbe98fe1bd86ee
Source dataset
uspto-grants-2008_12
Patent number
US07459453B2

Reaction notes

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