3-(1-hydroxy-ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester → Methyl 3-acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylate

HRID 240899

반응식

HRID 240899 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:13]([OH:15])[CH3:14])=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13](=[O:15])[CH3:14])=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4]

참가 물질

4

반응물 1

HCID 710141213-(1-hydroxy-ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester

생성물 1

HCID 71014110Methyl 3-acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylate수율 95%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

Reflux a mixture of 3-(1-Hydroxy-ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester (3.2 g, 0.0141 mol) and manganese dioxide (10.8 g, 0.124 mol) in dichloromethane for 2 hours. Filter the hot reaction mixture solution and concentrate the filtration under vacuum. Purify the residue by silica gel chromatograph (eluting with 2% to 10% ethyl acetate in petroleum ether) to give 3-acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester as white solid (3.0 g, 13.39 mmol, 94.5%). 1H NMR (CDCl3, 400 MHz): δ 3.88 (s, 3H), 2.96 (m, 4H), 2.50 (s, 3H), 2.45 (m, 2H).

후처리

  1. temperatureReflux
  2. filtrationFilter the hot reaction mixture solution
  3. concentrationconcentrate
  4. filtrationthe filtration under vacuum
  5. customPurify the residue
  6. washby silica gel chromatograph (eluting with 2% to 10% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-0a598e2595e94543909c752c77fbe76e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648081B2

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