Ammonium Chloride → 4-[(4E)-3-{3,5-difluoro-4-[(triisopropylsilyl)oxy]benzyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzonitrile

HRID 1921895노트

반응식

HRID 1921895 반응식
C([Li])CCC.[Br-].[OH:7][C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:34][C:35]1[CH:36]=[C:37]([CH:52]=[C:53]([F:66])[C:54]=1[O:55][Si:56]([CH:63]([CH3:65])[CH3:64])([CH:60]([CH3:62])[CH3:61])[CH:57]([CH3:59])[CH3:58])[CH2:38][CH:39]([CH:50]=O)[CH2:40][CH2:41][C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=1.[Cl-].[NH4+]>CCCCCC.C1COCC1>[F:34][C:35]1[CH:36]=[C:37]([CH:52]=[C:53]([F:66])[C:54]=1[O:55][Si:56]([CH:57]([CH3:59])[CH3:58])([CH:60]([CH3:62])[CH3:61])[CH:63]([CH3:65])[CH3:64])[CH2:38][CH:39](/[CH:50]=[CH:10]/[C:9]1[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=1[OH:7])[CH2:40][CH2:41][C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 579719344-[3-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)-4-oxobutyl]benzonitrileHCID 178418339Butyllithium

생성물 1

HCID 579719094-[(4E)-3-{3,5-difluoro-4-[(triisopropylsilyl)oxy]benzyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzonitrile

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

1.82 ml (2.91 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added to a solution of 579 mg (1.25 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 11.5 ml of THF at 0° C. Then, at this temperature, 490 mg (1.04 mmol) of 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-oxobutyl]benzonitrile are slowly metered in. The reaction solution is stirred at 0° C. for 2 h and then mixed with 100 ml of saturated ammonium chloride solution and extracted with diethyl ether. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 379.7 mg (54% of theory) of a colorless solid are obtained.

후처리

  1. extractionextracted with diethyl ether
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe solvent is concentrated to dryness
  6. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)
  7. custom379.7 mg (54% of theory) of a colorless solid are obtained

출처 및 근거

ORD 기록
ord-c3dcfcffcc4548a88733ee4a6a2611f2
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173704B2

반응 노트

불러오는 중…