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

HRID 361724

반응식

HRID 361724 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4bf5ba3413594603950397f523a48076
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866616

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