Sodium hydride → HCID 54574257、化合物

HRID 322992ノート

反応式

HRID 322992 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].Cl[CH:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]#[N:35])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C)C=O>[C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH:20]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:35]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10657149HCID 10657149、化合物HCID 53919123HCID 53919123、化合物

生成物 1

HCID 54574257HCID 54574257、化合物収率 5.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Hydroxy-4-(3-thienylmethoxy)benzonitrile (2.5 g) is added portionwise to a stirred suspension of sodium hydride (0.44 g, 60% dispersion in mineral oil) in dry dimethyl formamide (30 mL). After stirring at ambient temperature for 30 minutes, ethyl (RS)-4-chloro-4-(2-cyanophenyl)butanoate (2.87 g) is added in one portion and the reaction stirred for 16 hours at 100° C. The reaction is concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase is dried over magnesium sulphate, filtered and concentrated in vacuo. The residual oil is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2 v/v). Fractions homogeneous in the required product are combined and evaporated to give ethyl (RS)-4-(2-cyanophenyl)-4-[2-cyano-5-(3-thienylmethoxy)phenoxy]butanoate (250 mg) as an orange oil.

後処理

  1. stirringthe reaction stirred for 16 hours at 100° C
  2. concentrationThe reaction is concentrated in vacuo
  3. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual oil is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2 v/v)
  8. customevaporated

出典と根拠

ORDレコード
ord-bff197cd75244f6bba849616f024b7f3
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

反応ノート

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