Hexachloroethane → 2-(4-(2-Chloro-4-methyloxazol-5-yl)phenyl)-2-methylpropanenitrile

HRID 1672562노트

반응식

HRID 1672562 반응식
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][CH:15]=[N:14][C:13]=2[CH3:17])=[CH:8][CH:7]=1)([CH3:5])[C:3]#[N:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:28]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:28][C:15]1[O:16][C:12]([C:9]2[CH:8]=[CH:7][C:6]([C:2]([CH3:1])([CH3:5])[C:3]#[N:4])=[CH:11][CH:10]=2)=[C:13]([CH3:17])[N:14]=1

참가 물질

5

반응물 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 666966892-Methyl-2-(4-(4-methyloxazol-5-yl)phenyl)propanenitrile

생성물 1

HCID 666965992-(4-(2-Chloro-4-methyloxazol-5-yl)phenyl)-2-methylpropanenitrile수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Example 35C (2.35 g, 10.4 mmol) in THF (50 mL) at −78° C. was added LiHMDS (1.0 M in THF, 11.4 ml, 11.4 mmol) slowly via syringe. The solution was stirred 45 min, and then solid hexachloroethane (3.69 g, 15.6 mmol) was added in one portion. The reaction was allowed to proceed for 16 hr, gradually warming to ambient temperature. The reaction was quenched with half-saturated aq NH4Cl solution, and the product was extracted with Et2O. The combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280™; 0% to 20% EtOAc/hexanes eluant; SF40-150 g column) yielded 2.52 g (93%) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.66 (s, 4H), 2.36 (s, 3H), 1.71 (s, 6H). MS (DCI+) m/z 261 (M+H).

후처리

  1. waitto proceed for 16 hr
  2. customThe reaction was quenched with half-saturated aq NH4Cl solution
  3. extractionthe product was extracted with Et2O
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-64cbe38de9244e848c8d6049bedbcff8
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998993B2

반응 노트

불러오는 중…