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

HRID 343544

反応式

HRID 343544 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-030fb87aa11a4adf82f985093e9830a5
出典データセット
uspto-grants-1999_01
特許番号
US05861421

関連ノート

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