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

HRID 1672562ノート

反応式

HRID 1672562 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-64cbe38de9244e848c8d6049bedbcff8
出典データセット
uspto-grants-2011_08
特許番号
US07998993B2

反応ノート

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