Bromoacetonitrile → Ethyl 3-cyano-2-(4-(trifluoromethyl)phenyl)propanoate

HRID 1667291ノート

反応式

HRID 1667291 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:28][C:29]#[N:30]>O1CCCC1>[C:29]([CH2:28][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:15])([F:16])[F:1])=[CH:8][CH:7]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:30]

参加物

5

反応物 3

HCID 11534BromoacetonitrileHCID 2733832Lithium HexamethyldisilazideHCID 14134124Ethyl (4-(trifluoromethyl)phenyl)acetate

生成物 1

HCID 67360010Ethyl 3-cyano-2-(4-(trifluoromethyl)phenyl)propanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of the product from Example 266A (5.25 g, 23.0 mmol) in dry tetrahydrofuran at −78° C. was added lithium bis(trimethylsilyl)amide (1.0 M in hexane) (23.00 mL, 23.0 mmol) dropwise via syringe under nitrogen. The reaction was brought to 0° C. and stirred for one hour. The reaction was re-cooled to −78° C. and then bromoacetonitrile (1.56 mL, 23.0 mmol) was added as a solution in tetrahydrofuran (10 mL). The reaction was stirred for 2 hours while the temperature was allowed to reach room temperature. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organics were washed with brine, dried with MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (10% ethyl acetate/hexanes), to obtain the title compound. MS (DCI+) m/z 289 (M+NH4)+.

後処理

  1. customwas brought to 0° C.
  2. stirringThe reaction was stirred for 2 hours while the temperature
  3. customto reach room temperature
  4. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  5. extractionextracted with diethyl ether
  6. washThe organics were washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography (10% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-c26d5049539b4c03b932f0caef504953
出典データセット
uspto-grants-2011_10
特許番号
US08044069B2

反応ノート

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