Hydrochloric Acid → 6-Methoxybenzo[b]thiophene-2-ethanol

HRID 275743

반응식

HRID 275743 반응식
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[CH:14][S:13][C:12]=2[CH:16]=1.[CH2:17]1[O:19][CH2:18]1.Cl>O1CCCC1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[C:14]([CH2:17][CH2:18][OH:19])[S:13][C:12]=2[CH:16]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 136342376-Methoxy-1-benzothiopheneHCID 178418339Butyllithium

생성물 1

HCID 235006406-Methoxybenzo[b]thiophene-2-ethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-30 °C

실험 절차

Butyl lithium (0.27 mol of a 2.5 M solution) was added dropwise to 6-methoxybenzo[b]thiophene [prepared analogous to the procedure described in J. Med. Chem. 1989, 32(12), 2548-2554] (0.25 mol) in tetrahydrofuran (1000 ml), stirred at −30° C. The mixture was stirred for 10 minutes at −30° C. Ethylene oxide (0.38 mol in 100 ml tetrahydrofuran) was added dropwise at −30° C. The mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was acidified with dilute HCl solution. The solvent was evaporated. The residue was diluted with water and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was stirred in hexane, filtered off and dried, yielding 41.3 g of 6-methoxybenzo[b]thiophene-2-ethanol (interm. 2).

후처리

  1. customprepared analogous to the procedure
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 hours
  4. customThe solvent was evaporated
  5. additionThe residue was diluted with water
  6. extractionthis mixture was extracted with CH2Cl2
  7. customThe separated organic layer was dried
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. stirringThe residue was stirred in hexane
  11. filtrationfiltered off
  12. customdried

출처 및 근거

ORD 기록
ord-4653e6bd356b45a5af963add539b691f
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352999B1

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