Propylethinylcarbinol → (1-Ethynylbutoxy)acetic Acid Ethyl Ester

HRID 18822

反応式

HRID 18822 の反応式
[CH:1]#[C:2][CH:3]([OH:7])[CH2:4][CH2:5][CH3:6].[N+](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][O:7][CH:3]([C:2]#[CH:1])[CH2:4][CH2:5][CH3:6])[CH3:15]

参加物

6

反応物 2

HCID 7746PropylethinylcarbinolHCID 12192Ethyl diazoacetate

生成物 1

HCID 86140139(1-Ethynylbutoxy)acetic Acid Ethyl Ester収率 54.3%

試薬・触媒・溶媒 3

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒HCID 8900Heptane溶媒

実験手順

To a solution of 1-hexyn-3-ol (981 mg, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (1.0 mL, 9.0 mmol). The reaction mixture is stirred at rt for 6 h. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel: elution with EtOAc:heptane (25:75) gives 900 mg of the product 446. 1H NMR (CDCl3) δ 4.35-4.10 (m, 5 H), 2.43 (s, 1 H), 1.90-1.65 (m, 2 H), 1.65-1.40 (m, 2 H), 1.40-1.20 (m, 3 H), 0.95 (t, 3 H)

後処理

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. customthe residue purified by chromatography on silica gel
  4. washelution with EtOAc:heptane (25:75)

出典と根拠

ORDレコード
ord-8bf3d22982394b67b3c5d92fe4440613
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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