Pyridine → (RS)-3-(2-propenyl)-3-cyclopenten-1-yl (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

HRID 582733ノート

反応式

HRID 582733 の反応式
[CH2:1]([C:4]1[CH2:5][CH:6]([OH:9])[CH2:7][CH:8]=1)[CH:2]=[CH2:3].N1C=CC=CC=1.[CH3:16][C:17]1([CH3:27])[C@H:19]([CH:20]=[C:21]([CH3:23])[CH3:22])[C@H:18]1[C:24](Cl)=[O:25]>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C1(C)C=CC=CC=1>[CH3:16][C:17]1([CH3:27])[C@H:19]([CH:20]=[C:21]([CH3:22])[CH3:23])[C@H:18]1[C:24]([O:9][CH:6]1[CH2:7][CH:8]=[C:4]([CH2:1][CH:2]=[CH2:3])[CH2:5]1)=[O:25]

参加物

6

反応物 3

HCID 1049PyridineHCID 10867076(1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarbonyl chlorideHCID 53659626(RS)-3-allyl-3-cyclopenten-1-ol

生成物 1

HCID 53684856(RS)-3-(2-propenyl)-3-cyclopenten-1-yl (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate収率 65.6%

試薬・触媒・溶媒 2

HCID 314042,6-Di-tert-butyl-4-methylphenol触媒HCID 1140Toluene溶媒

実験手順

To a mixture of (RS)-3-(2-propenyl)-3-cyclopenten-1-ol (115 mg), 2,6-di-tert-butyl-4-methylphenol (5 mg), pyridine (5 mg) and toluene (5 ml), (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarbonyl chloride (171 mg) was added under ice-cooling. The resulting reaction mixture was further allowed to react for 8 hours at room temperature. Then the reaction mixture was subjected to the same post-treatment as in Example 1 to afford 165 mg of (RS)-3-(2-propenyl)-3-cyclopenten-1-yl (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (Compound No. 41). Yield 65% DD27 1.4895

後処理

  1. additionwas added under ice-
  2. temperaturecooling
  3. customThe resulting reaction mixture
  4. customto react for 8 hours at room temperature

出典と根拠

ORDレコード
ord-d676dfcef819473f9847cb95d891a587
出典データセット
uspto-grants-1999_07
特許番号
US05925676

反応ノート

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