Hydrochloric Acid → 2-Benzyl-benzo[b]thiophene-3-carboxaldehyde

HRID 1280902노트

반응식

HRID 1280902 반응식
[Sn](Cl)(Cl)(Cl)Cl.[CH2:6]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:22][O:23]C(Cl)Cl.Cl>ClCCl>[CH2:6]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[C:14]=1[CH:22]=[O:23])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 127581572-Benzyl-1-benzothiophene

생성물 1

HCID 234456472-Benzyl-benzo[b]thiophene-3-carboxaldehyde수율 85.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Tin chloride (14.0 mL, 119.6 mmol) was added dropwise into a cold (−20° C.) solution of 2-benzyl-benzo[b]thiophene (13.4 g, 59.8 mmol) in dichloromethane (150.0 mL). After 1 h, to the reaction was added dropwise dichloromethyl methyl ether (119.6 mmol). The mixture was allowed to gradually come to 0° C., and then stirred for 20 hours. The mixture was carefully poured into HCl (2 N) and ice, and extracted with ethyl ether. The ethereal extracts were dried (MgSO4) and concentrated to give 12.9 g (85%) of the title compound after crystallization from ethyl ether/hexanes, yellow solid mp 86-88° C.; mass spectrum m/z 252 (M+). Anal. Calcd. for C16H12O5: C 76.16; H, 4.79. Found: C, 75.77; H, 4.85

후처리

  1. customto gradually come to 0° C.
  2. extractionextracted with ethyl ether
  3. dry with materialThe ethereal extracts were dried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-037fd4997fe347d3adf3c1d947d0c485
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451845B1

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