Phenylacetyl chloride → 3-Oxo-4-phenylbutanenitrile
反応式
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[Li]CCCC.[C:12]1([CH2:18]C(Cl)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[O:6]=[C:4]([CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:1]#[N:2]参加物
5
実験手順
To a solution of cyanoacetic acid (2 g, 23.5 mmol) in THF (100 mL) at −78° C. was added nBuLi (10 mL, 25.9 mmol, 2.5M in hexanes). After 30 min, phenylacetyl chloride (1.6 mL, 11.8 mmol) was added dropwise. Following an additional 30 min, the solution was partitioned between 1N HCl-Et2O and the aqueous phase was washed several times with Et2O. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 30% EtOAc in hexanes) yielding the title compound (770 mg, 40%) as a tan oil: LCMS (ES) m/z 160 (M+H)+.
後処理
- waitFollowing an additional 30 min
- customthe solution was partitioned between 1N HCl-Et2O
- washthe aqueous phase was washed several times with Et2O
- dry with materialThe combined organic fractions were dried over Na2SO4
- concentrationconcentrated
- custompurified via column chromatography (silica, 30% EtOAc in hexanes)
出典と根拠
- ORDレコード
- ord-cadee10fd3b34124a87c47e04302ddbc
- 出典データセット
- uspto-grants-2013_04
- 特許番号
- US08410158B2
反応ノート
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