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1-Methylimidazole → HCID 22714354, 화합물

HRID 852276
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HRID 852276 반응식
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
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참가 물질

6

반응물 4

HCID 13901-MethylimidazoleHCID 13819ChlorotriethylsilaneHCID 22136476(4-Chlorophenyl)[3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl]methanoneHCID 178418339Butyllithium2회

생성물 1

HCID 22714354HCID 22714354, 화합물수율 25%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

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온도
-70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b085b5043a414857b286a24d8796d995
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07253183B2

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