Dimethylformamide → 3-(3-Cyclopentyloxy methoxyphenyl)-3-ethynylcyclohexan-1-one

HRID 443201

Reaction equation

HRID 443201 reaction equation
[F-].[K+].[CH:3]1([O:8][C:9]2[CH:10]=[C:11]([C:17]3([C:24]#[C:25][Si](C)(C)C)[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18]3)[CH:12]=[CH:13][C:14]=2OC)CCCC1.CN(C)[CH:32]=[O:33]>>[CH:32]1([O:33][CH2:3][O:8][C:9]2[CH:10]=[C:11]([C:17]3([C:24]#[CH:25])[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18]3)[CH:12]=[CH:13][CH:14]=2)[CH2:13][CH2:14][CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 539837473-(3-Cyclopentyloxy-4-methoxyphenyl)-3-trimethylsilylethynylcyclohexan-1-one

Product 1

HCID 537691363-(3-Cyclopentyloxy methoxyphenyl)-3-ethynylcyclohexan-1-one

Procedure

A mixture of potassium fluoride (900 mg, 15.6 mmol) and 3-(3-cyclopentyloxy-4-methoxyphenyl)3-trimethylsilylethynyl cyclohexan-1-one (0.3 g, 0.78 mmol) was stirred in dry N,N-dimethylformamide (3 mL) under an argon atmosphere. After 18 h, the solvent was removed in vacuo, the residue was partitioned between water and ethyl acetate, the aqueous layer was extracted twice with ethyl acetate, the combined extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 4:1 hexanes/ethyl acetate provided a clear colorless oil . Anal. (C20H24O3 ·1/10H2O) calcd: C 76.45,H 7.76; found: C 76.32,H 7.60.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. extractionthe combined extract
  5. dry with materialwas dried (magnesium sulfate)
  6. customwas evaporated
  7. customPurification by flash chromatography
  8. washeluting with 4:1 hexanes/ethyl acetate
  9. customprovided a clear colorless oil

Sources & evidence

ORD record
ord-2a9161eed8084afc9d4b632dfb550c5f
Source dataset
uspto-grants-1999_04
Patent number
US05892098

Linked notes

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