Methanol → 2-Cyclopenten-1-one, 2-pentyl-

HRID 615461ノート

反応式

HRID 615461 の反応式
C(O[C:5]([C:13]#[CH:14])([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:6]=[CH2:7])(=O)C.CO.CCCCC.CC[O:24]CC.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(O)(=O)C.CN(C)C1C=CN=CC=1>[CH2:8]([C:5]1[C:6](=[O:24])[CH2:7][CH2:14][CH:13]=1)[CH2:9][CH2:10][CH2:11][CH3:12]

参加物

8

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 13234852HCID 13234852、化合物HCID 21877078Diethylether pentane

生成物 1

HCID 1175492-Cyclopenten-1-one, 2-pentyl-収率 66%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 184 mg (0.95 mM) of 1-ethynyl-1-pentyl-2-propenyl acetate and 13 mg (0.05 mM) of PdCl2 (CH3CN)2 in 1.2 ml of acetonitrile and 60 μl of glacial acetic acid was heated at 80° during 2 h. 1 Ml of methanol and some crystals of 4-dimethylaminopyridine were added to the reaction mixture and the whole was stirred for 45 minutes at room temperature, whereupon 10 ml of a 1:1 mixture of pentane/ether were added followed by a small quantity of potassium carbonate. The reaction mixture was then stirred for 30 minutes, it was then filtered and evaporated. The obtained residue gave by bulb to bulb distillation 104 mg of a colorless distillate constituted by the desired product having a purity of 92% (yield 66%). By carrying out the reaction in toluene instead of acetonitrile at a temperature of about 80°, the desired product was obtained, though in lower yields.

後処理

  1. temperaturewas heated at 80° during 2 h
  2. additionwere added
  3. filtrationit was then filtered
  4. customevaporated
  5. customThe obtained residue gave by bulb to bulb distillation 104 mg of a colorless distillate

出典と根拠

ORDレコード
ord-7feb456230eb48559cbe467f6f5a9424
出典データセット
uspto-grants-1985_02
特許番号
US04499297

反応ノート

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