Pyridine → 4-Methylocta-4-ene-1,7-diyne-3-yl alpha-isopropyl-4-chlorophenylacetate

HRID 372474

反応式

HRID 372474 の反応式
[CH3:1][C:2](=[CH:7][CH2:8][C:9]#[CH:10])[CH:3]([OH:6])[C:4]#[CH:5].N1C=CC=CC=1.[CH:17]([CH:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:21](Cl)=[O:22])([CH3:19])[CH3:18]>C1C=CC=CC=1>[CH:17]([CH:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:21]([O:6][CH:3]([C:2]([CH3:1])=[CH:7][CH2:8][C:9]#[CH:10])[C:4]#[CH:5])=[O:22])([CH3:19])[CH3:18]

参加物

5

反応物 3

HCID 1049Pyridine2 回HCID 41780012-(4-Chlorophenyl)-3-methylbutanoyl chlorideHCID 54236197HCID 54236197、化合物

生成物 1

HCID 542319964-Methylocta-4-ene-1,7-diyne-3-yl alpha-isopropyl-4-chlorophenylacetate収率 85.1%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

1.40 Grams (11.4 millimoles) of 4-methylocta-4-ene-1,7-diyne-3-ol is dissolved in 20 ml of a dry benzene, followed by cooling in ice water. Thereafter, 1.80 g (22.8 millimoles) of pyridine is rapidly added thereto at a time and immediately a solution of 2.64 g (11.4 millimoles) of α-isopropyl-4-chlorophenylacetyl chloride in 10 ml of dry benzene is dropwise added thereto for about 30 minutes with stirring. After completion of the addition, stirring is continued for 3 hours at room temperature to complete the reaction. The reaction mixture is poured into 20 g of ice water and the layers are separated. The aqueous layer is extracted with two 10-ml portions of ether. The organic layers obtained is combined and washed once with a 10% hydrochloric acid and three times with water, followed by drying over anhydrous sodium sulfate. After the solvent is removed under reduced pressure, the oily substance obtained is mixed with almost the same amount of pyridine. The mixture is adsorbed to 100 g of silica gel column and purified by developing with a mixed solvent (18 : 1 : 1) of carbon tetrachloride : n-hexane : ether. Thus, 3.19 g of the objective ester is obtained as a pale yellow oily substance (85.1% of theoretical yield). nD23.0 1.5233

後処理

  1. additionAfter completion of the addition
  2. stirringstirring
  3. waitis continued for 3 hours at room temperature
  4. customthe reaction
  5. customthe layers are separated
  6. extractionThe aqueous layer is extracted with two 10-ml portions of ether
  7. customThe organic layers obtained
  8. washwashed once with a 10% hydrochloric acid and three times with water
  9. dry with materialby drying over anhydrous sodium sulfate
  10. customAfter the solvent is removed under reduced pressure
  11. customthe oily substance obtained
  12. custompurified

出典と根拠

ORDレコード
ord-e75b1ebc56484f50a4c8b2da4711173d
出典データセット
uspto-grants-1978_05
特許番号
US04091111

関連ノート

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