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1-Methylimidazole → HCID 22714354、化合物

HRID 351786
ノート
印刷プレビュー

反応式

HRID 351786 の反応式
C([Li])CCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.Cl[Si](CC)(CC)CC.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:29]2[CH:30]=[CH:31][C:32]3[C:33]([CH:44]=2)=[C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[O:35][N:36]=3)=[O:28])=[CH:23][CH:22]=1>C1COCC1>[Cl:43][C:39]1[CH:38]=[C:37]([C:34]2[O:35][N:36]=[C:32]3[CH:31]=[CH:30][C:29]([C:27]([C:24]4[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][CH:25]=4)([C:11]4[N:7]([CH3:6])[CH:8]=[N:9][CH:10]=4)[OH:28])=[CH:44][C:33]=23)[CH:42]=[CH:41][CH:40]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 13901-MethylimidazoleHCID 13819ChlorotriethylsilaneHCID 22136476(4-Chlorophenyl)[3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl]methanoneHCID 178418339Butyllithium2 回

生成物 1

HCID 22714354HCID 22714354、化合物収率 25%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
-70 °C

実験手順

Butyllithium in hexanes (10 ml) was added slowly at −70° C. under N2 flow to a solution of 1-methylimidazole (1.31 g) in THF (30 ml). The mixture was stirred at −70° C. for 45 minutes. Chlorotriethylsilane (2.7 ml) was added. The mixture was allowed to warm to 15° C. and cooled to −70° C. Butyllithium (10 ml) was added slowly. The mixture was stirred at −70° C. for 1 hour, allowed to warm to −15° C. and cooled to −70° C. A solution of intermediate (6-b) (4.9 g) in THF (60 ml) was added. The mixture was stirred at −70° C. for 30 minutes, then hydrolyzed with water, extracted with ethyl acetate and decanted. The organic layer was dried, filtered and the solvent was evaporated. The residue (8.2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.2) and crystallized from 2-propanone/diethyl ether. The precipitate was filtered off and dried, yielding 1.5 g (25%) of (±)-3-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-2,1-benzisoxazole-5-methanol (interm. 6-c).

後処理

  1. temperatureto warm to 15° C.
  2. temperaturecooled to −70° C
  3. stirringThe mixture was stirred at −70° C. for 1 hour
  4. temperatureto warm to −15° C.
  5. temperaturecooled to −70° C
  6. stirringThe mixture was stirred at −70° C. for 30 minutes
  7. extractionhydrolyzed with water, extracted with ethyl acetate
  8. customdecanted
  9. customThe organic layer was dried
  10. filtrationfiltered
  11. customthe solvent was evaporated
  12. customThe residue (8.2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.2)
  13. customcrystallized from 2-propanone/diethyl ether
  14. filtrationThe precipitate was filtered off
  15. customdried

出典と根拠

ORDレコード
ord-a96c32fd8b054e6ba26da5b965c82eb8
出典データセット
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06743805B2

反応ノート

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