Sodium borohydride → 6-Bromo-2,2-dimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxide

HRID 2390294ノート

反応式

HRID 2390294 の反応式
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6](=[O:13])[C:7]([CH3:12])([CH3:11])[S:8](=[O:10])(=[O:9])[C:4]=2[CH:3]=1.[BH4-].[Na+]>CO.C(Cl)Cl>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]([OH:13])[C:7]([CH3:11])([CH3:12])[S:8](=[O:9])(=[O:10])[C:4]=2[CH:3]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 565941096-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide2 回

生成物 1

HCID 565941116-Bromo-2,2-dimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxide収率 97.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A cooled (0° C.) solution of 6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide (Intermediate 241; 652 mg; 2.25 mmol) in MeOH (15 ml) and DCM (7 ml) was treated with NaBH4 (43 mg; 1.13 mmol) portionwise. The resulting solution was stirred at RT for 1.5 h, before being cooled to 0° C. and carefully quenched with water. The mixture was concentrated under reduced pressure, water was added to the residue and the aqueous phase was extracted three times with DCM. The combined organic phases were washed with brine, dried with MgSO4, filtered and concentrated to dryness to give the title compound as a white solid (637 mg, 97%).

後処理

  1. temperaturebefore being cooled to 0° C.
  2. customcarefully quenched with water
  3. concentrationThe mixture was concentrated under reduced pressure, water
  4. additionwas added to the residue
  5. extractionthe aqueous phase was extracted three times with DCM
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-733b391bbf2c4ad7b887ec3645f502cf
出典データセット
uspto-grants-2012_09
特許番号
US08273769B2

反応ノート

読み込み中…