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

HRID 275743

反応式

HRID 275743 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4653e6bd356b45a5af963add539b691f
出典データセット
uspto-grants-2002_03
特許番号
US06352999B1

関連ノート

読み込み中…