Water → 3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one

HRID 1308

Reaction equation

HRID 1308 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]=2[O:15][CH3:16])[CH2:7][CH2:6][CH2:5][CH2:4]1.O>CN(C)C=O>[CH:3]1([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][C:14]=2[O:15][CH3:16])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 522689Potassium FluorideHCID 539837473-(3-Cyclopentyloxy-4-methoxyphenyl)-3-trimethylsilylethynylcyclohexan-1-one

Product 1

HCID 153920073-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium fluoride (900 mg, 15.6 mmol) and 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-trimethylsilylethynylcyclohexan-1-one (0.3 g, 0.78 mmol) were 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. (C20H24O3.1/10 H2O) 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-a765bb3f88ef412dab87283ec66e35db
Source dataset
uspto-grants-1998_03
Patent number
US05723681

Linked notes

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