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4-Cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone → 1-(4-Cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol

HRID 278184
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HRID 278184 반응식
[C:1]1([C:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[CH:12]=[C:11]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([F:23])[CH:16]=3)=[O:14])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:36][Mg+].[Br-]>C1COCC1.CCOCC>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:13]([C:11]2[N:10]=[CH:9][N:8]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:12]=2)([OH:14])[CH3:36])=[CH:16][C:17]=1[F:23])#[N:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 545629854-Cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketoneHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 184336071-(4-Cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone from Step E (7.0 g, 15.3 mmol) in dry THF (280 mL), under argon, at −78° C., was added MeMgBr (5.3 mL of a 3.0 M solution in Et2O, 15.9 mmol), dropwise. After 1 hr, the reaction mixture was quenched with sat. aq. NH4Cl (100 mL) and extracted with CH2Cl2 (2×150 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of hexane—30% to 50% EtOAc, to yield the titled product as pale solid.

후처리

  1. customthe reaction mixture was quenched with sat. aq. NH4Cl (100 mL)
  2. extractionextracted with CH2Cl2 (2×150 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of hexane—30% to 50% EtOAc

출처 및 근거

ORD 기록
ord-8e6831451d4347779cda1f3c884a7951
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06358985B1

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