Benzonitrile, m-chloro- → Methyl 2-(2-chloro-4-cyanophenyl)acetate

HRID 923247

반응식

HRID 923247 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:20]([C:22]([O:24][CH3:25])=[O:23])#N>C1COCC1>[CH3:25][O:24][C:22](=[O:23])[CH2:20][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Cl:1]

참가 물질

5

반응물 3

HCID 13015Benzonitrile, m-chloro-HCID 28660Carbonocyanidic acid, methyl esterHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 86611068Methyl 2-(2-chloro-4-cyanophenyl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

4-{5-[2-tert-Butyldimethylsilanyloxy)ethyl]imidazol-1-ylmethyl}-3-chlorobenzonitrile (1.7 g, 4.52 mmol) is dissolved in anhydrous THF (30 mL) and stirred at −78° C. before a THF solution of LHMDS (8.1 mL, 1.0 M) is added. After 15 min, methyl cyanoformate (0.38 mL, 4.74 mmol) is added and the solution is left at −78° C. for 2 h. The excess LHMDS is quenched with aqueous saturated NH4Cl and the mixture is allowed to warm to room temperature. The mixture is then diluted with EtOAc and washed with aqueous saturated NH4Cl (2×). Organic is dried (Na2SO4) and evaporated. The crude residue is purified via flash column chromatography (EtOAc/hexanes 1:1→EtOAc) to give {5-[2-tert-butyldimethylsilanyloxy)ethyl]-imidazol-1-yl}-(2-chloro-4-cyanophenyl)acetic acid methyl ester as an oil. MS (ESI) m/z 434.3, 436.3 (M+H).

후처리

  1. additionis added
  2. waitthe solution is left at −78° C. for 2 h
  3. customThe excess LHMDS is quenched with aqueous saturated NH4Cl
  4. additionThe mixture is then diluted with EtOAc
  5. washwashed with aqueous saturated NH4Cl (2×)
  6. dry with materialOrganic is dried (Na2SO4)
  7. customevaporated
  8. customThe crude residue is purified via flash column chromatography (EtOAc/hexanes 1:1→EtOAc)

출처 및 근거

ORD 기록
ord-3b344fb1028c4a3381ec82f9efa63bb8
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278969B2

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