Water → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

HRID 343544

반응식

HRID 343544 반응식
[N+](=[CH:3]P(=O)(OC)OC)=[N-].CC(C)([O-])C.[K+].[CH:16]1([O:21][C:22]2[CH:23]=[C:24]([C:30]3([CH:40]=O)[CH2:35][CH2:34][C:33]4([O:39][CH2:38][CH2:37][O:36]4)[CH2:32][CH2:31]3)[CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[CH2:20][CH2:19][CH2:18][CH2:17]1.O>O1CCCC1>[CH:16]1([O:21][C:22]2[CH:23]=[C:24]([C:30]3([C:40]#[CH:3])[CH2:31][CH2:32][C:33]4([O:36][CH2:37][CH2:38][O:39]4)[CH2:34][CH2:35]3)[CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH2:20]1

참가 물질

6

반응물 4

HCID 962WaterHCID 5115033Dimethyl (diazomethyl)phosphonateHCID 153920374-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-formylcyclohexaneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 110895964-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of dimethyl (diazomethyl)phosphonate (0.516 g, 3.44 mmole, prepared as in Seyferth, D.; Marmor, R. S.; Hilbert, P. J. Org. Chem 1971, 36(10), 1379-1386) dissolved in dry tetrahydrofuran (10 mL) was added via cannulation to a solution of potassium t-butoxide (0.386 g, 3.4 mmol) dissolved in dry tetrahydrofuran (10 mL) at -78° C. under an argon atmosphere. To this was added rapidly a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-formylcyclohexane (0.62 g, 1.72 mmol) in dry tetrahydrofuran (10 mL). After 2 h, the reaction was warmed to room temperature, water was added and the mixture was extracted three times with ethyl acetate. The combined organic extract was washed with brine, was dried (sodium sulfate) and was evaporated. Purification by flash chromatography, eluting with 3:1 hexanes/ethyl acetate provided a white solid. mp 53.5°-55° C.

후처리

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialwas dried (sodium sulfate)
  5. customwas evaporated
  6. customPurification by flash chromatography
  7. washeluting with 3:1 hexanes/ethyl acetate
  8. customprovided a white solid

출처 및 근거

ORD 기록
ord-030fb87aa11a4adf82f985093e9830a5
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861421

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