Propylethinylcarbinol → (1-Ethynylbutoxy)acetic Acid Ethyl Ester

HRID 18822

반응식

HRID 18822 반응식
[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]

참가 물질

6

반응물 2

HCID 7746PropylethinylcarbinolHCID 12192Ethyl diazoacetate

생성물 1

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

시약·촉매·용매 3

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 6344Dichloromethane용매HCID 8900Heptane용매

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-8bf3d22982394b67b3c5d92fe4440613
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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