Methanol → 5-Carboxy-3-(2,4-dichlorobenzyl)-2-methylbenzo[b]thiophene

HRID 1699854노트

반응식

HRID 1699854 반응식
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[C:6]2[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[CH:12]=[CH:11][C:7]=2[S:8][C:9]=1[CH3:10].CO.[OH-].[Na+]>O1CCCC1>[C:15]([C:13]1[CH:12]=[CH:11][C:7]2[S:8][C:9]([CH3:10])=[C:5]([CH2:4][C:3]3[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:2]=3[Cl:1])[C:6]=2[CH:14]=1)([OH:17])=[O:16]

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 223881313-(2,4-Dichlorobenzyl)-5-(methoxycarbonyl)-2-methylbenzo[b]thiophene

생성물 1

HCID 223878405-Carboxy-3-(2,4-dichlorobenzyl)-2-methylbenzo[b]thiophene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 3-(2,4-Dichlorobenzyl)-5-(methoxycarbonyl)-2-methylbenzo-[b]thiophene (0.52 g, 1.42 mmol), methanol (5 ml), tetrahydrofuran (5 ml) and 2 ml aqueous sodium hydroxide solution (7 ml) was refluxed under heating for 1 hr. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. Then, the mixture was acidified with 3N hydrochloric acid and the precipitate was extracted from hot ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The desiccant was ffitered off, and the filtrate was concentrated under reduced pressure to give the objective compound (0.45 g, 90% by two steps) as colorless crystals.

후처리

  1. temperaturewas refluxed
  2. temperatureunder heating for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionthe precipitate was extracted from hot ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customto give the objective compound (0.45 g, 90% by two steps) as colorless crystals

출처 및 근거

ORD 기록
ord-36fd64d3a8c14f61bfd76326dbd05c21
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348474B1

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