Methanol → 2-(4-Chlorophenyl)tetrahydro-2-furancarboxylic acid

HRID 2229484노트

반응식

HRID 2229484 반응식
[C-]#N.[K+].Cl[CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:9].[OH2:17].[CH3:18][OH:19]>>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2([C:18]([OH:19])=[O:17])[CH2:7][CH2:6][CH2:5][O:9]2)=[CH:11][CH:12]=1

참가 물질

5

반응물 4

HCID 887MethanolHCID 962WaterHCID 9032Potassium CyanideHCID 27237814,4'-Dichlorobutyrophenone

생성물 1

HCID 184678832-(4-Chlorophenyl)tetrahydro-2-furancarboxylic acid

실험 절차

Potassium cyanide (1.87 g, 28.78 mmol) was added to a solution of 4-chloro-4′-chloro-butyrophenone (5.00 g, 23.03 mmol) in 25 mL of methanol. After stirring for 3 days at room temperature, the reaction was poured into water (50 mL) and extracted with methylene chloride (3×50 mL). The organic layers were combined, washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (Biotage) over silica gel eluting with hexane/ethyl acetate (30:1) to give 3.52 g of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ 7.47 (m, 2H); 7.38 (m, 2H); 4.24 (m, 2H); 2.74 (m, 1H); 2.33 (m, 1H), 2.15 (m, 2H).

후처리

  1. extractionextracted with methylene chloride (3×50 mL)
  2. washwashed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (Biotage) over silica gel eluting with hexane/ethyl acetate (30:1)

출처 및 근거

ORD 기록
ord-3b26ffa5124247f5a2f2a65c1cca4403
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06420418B1

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