Acetonitrile → Methyl (RS)-4-cyano-2-phenylbutanoate

HRID 486487

反応式

HRID 486487 の反応式
C([N-]C(C)C)(C)C.[Li+].[C:9](#[N:11])[CH3:10].[C:12]1([C:18](=[CH2:23])[C:19]([O:21][CH3:22])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>C1CCCCC1.O1CCCC1>[C:9]([CH2:10][CH2:23][CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:19]([O:21][CH3:22])=[O:20])#[N:11]

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 25517Ammonium ChlorideHCID 193334Methyl atropateHCID 2724682Lithium diisopropylamide

生成物 1

HCID 53645094Methyl (RS)-4-cyano-2-phenylbutanoate収率 75%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8078Cyclohexane溶媒

実験手順

Lithium diisopropylamide (3.67 ml of a 1.5 molar solution in cyclohexane) was added to acetonitrile (0.26 ml) in tetrahydrofuran (10 ml) at -78° C. After 1 hour, methyl 2-phenyl-acrylate (see Preparation 22) (0.81 g) in tetrahydrofurn (10 ml) was added and the mixture was stirred for 1 hour, allowed to warm to room temperature then treated with saturated ammonium chloride solution. The resulting mixture was partitioned between ethyl acetate and water, the organic phase dried over magnesium sulphate and evaporated to give a residue which was partitioned between ether and 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulphate and evaporated to leave the title compound (0.5 g, 75%) as an oil.

後処理

  1. customThe resulting mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organic phase dried over magnesium sulphate
  3. customevaporated
  4. customto give a residue which
  5. customwas partitioned between ether and 10% aqueous sodium carbonate
  6. dry with materialThe organic layer was dried over magnesium sulphate
  7. customevaporated

出典と根拠

ORDレコード
ord-80af75f55504407f8422051aeb00f6fc
出典データセット
uspto-grants-1994_03
特許番号
US05292749

関連ノート

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