3-Bromothiophene → 1-butyl-alpha-(3-thienyl)-1H-benzotriazole-5-methanol

HRID 2166040ノート

反応式

HRID 2166040 の反応式
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.C([Li])CCC.[CH2:12]([N:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]=[O:26])=[CH:24][C:19]=2[N:18]=[N:17]1)[CH2:13][CH2:14][CH3:15]>CCCCCC.O(CC)CC>[CH2:12]([N:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]([C:2]3[CH:6]=[CH:5][S:4][CH:3]=3)[OH:26])=[CH:24][C:19]=2[N:18]=[N:17]1)[CH2:13][CH2:14][CH3:15]

参加物

6

反応物 3

HCID 133833-BromothiopheneHCID 14990615butyl-1H-benzotriazole-5-carboxaldehydeHCID 178418339Butyllithium

生成物 1

HCID 149906161-butyl-alpha-(3-thienyl)-1H-benzotriazole-5-methanol収率 58.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

To a stirred and cooled (-78° C.) solution of 7.2 parts of 3-bromothiophene in 70 parts of 1,1'-oxybisethane were added 30 parts of a 1-butyllithium solution 1.6M in hexane. After stirring for 20 minutes at this low temperature, a solution of 6 parts of 1-butyl-1H-benzotriazole-5-carboxaldehyde in 1,1'-oxybisethane was added to the previous mixture. The reaction mixture was stirred for 2 hours at -78°~-'° C. The whole was poured into 200 parts of ice water and the product was extracted three times with 56 parts of 1,1'-oxybisethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 5 parts (58.9%) of 1-butyl-α-(3-thienyl)-1H-benzotriazole-5-methanol; mp. 80° C. (int. 58).

後処理

  1. stirringAfter stirring for 20 minutes at this low temperature
  2. stirringThe reaction mixture was stirred for 2 hours at -78°~-'° C
  3. extractionthe product was extracted three times with 56 parts of 1,1'-oxybisethane
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 2,2'-oxybispropane
  12. filtrationThe product was filtered off
  13. customdried

出典と根拠

ORDレコード
ord-e1f17b5424a34446b5cdff468b9d9c8a
出典データセット
uspto-grants-1990_07
特許番号
US04943574

反応ノート

読み込み中…