Pyridine → (9,10-Dihydro-1-phenanthryl)methyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 2164844ノート

反応式

HRID 2164844 の反応式
[C:1]1([CH2:15][OH:16])[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:23][C:24]([Cl:34])=[CH:25][C@@H:26]1[C@H:28]([C:29](Cl)=[O:30])[C:27]1([CH3:33])[CH3:32]>C1C=CC=CC=1>[Cl:23][C:24]([Cl:34])=[CH:25][C@@H:26]1[C@H:28]([C:29]([O:16][CH2:15][C:1]2[C:14]3[CH2:13][CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[CH:4]=[CH:3][CH:2]=2)=[O:30])[C:27]1([CH3:32])[CH3:33]

参加物

5

反応物 3

HCID 1049PyridineHCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chlorideHCID 132813369,10-Dihydrophenanthrene-1-methanol

生成物 1

HCID 86739266(9,10-Dihydro-1-phenanthryl)methyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

A mixture of 9,10-dihydrophenanthrene-1-methanol (0.5 gram, 0.0024 mole) and pyridine (1 gram, 0.013 mole) in benzene (25 ml) was added to a stirred solution of cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (0.7 gram, 0.0031 mole) in benzene (25 ml). The mixture was stirred at room temperature for 2.5 days, then partitioned between water (80 ml) and diethyl ether (50 ml). The organic phase was separated and washed consecutively with water, 10% aqueous sodium carbonate and water. The organic phase was then dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to give a yellow oil. The oil was purified by chromatography on silica gel to give (9,10-dihydro-1-phenanthryl)methyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate as an oil.

後処理

  1. custompartitioned between water (80 ml) and diethyl ether (50 ml)
  2. customThe organic phase was separated
  3. washwashed consecutively with water, 10% aqueous sodium carbonate and water
  4. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customto give a yellow oil
  8. customThe oil was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-25b4a4233ea14ce8a2c0fd85ef2edffa
出典データセット
uspto-grants-1985_03
特許番号
US04507317

反応ノート

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