Sodium hydride → HCID 53853519、化合物

HRID 322976ノート

反応式

HRID 322976 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]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=1[CH3:35])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)=[CH:9][C:2]=1[O:1][CH:20]([C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=1[CH3:35])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:5]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10657149HCID 10657149、化合物HCID 54337869HCID 54337869、化合物

生成物 1

HCID 53853519HCID 53853519、化合物収率 17.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Hydroxy-4-(3-thienylmethoxy)benzonitrile (1.5 g) is added portionwise to a stirred suspension of sodium hydride (440 mg, 60% dispersion in mineral oil) in dry DMF(50 mL). After stirring at ambient temperature for 30 minutes, ethyl (RS)-4-chloro-4-(2,5-dimethylphenyl)butanoate (2.5 g) is added in one portion and the reaction stirred for 48 hours at 90° C. The reaction is concentrated in vacuo and the residue partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer is extracted twice with ethyl acetate (50 mL). The combined organic phases are dried over magnesium sulphate, filtered and concentrated in vacuo. The residue 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-cyano-5-(3-thienylmethoxy)phenoxy)-4-(2,5-dimethylphenyl)butanoate (500 mg) as a pale brown oil.

後処理

  1. stirringthe reaction stirred for 48 hours at 90° C
  2. concentrationThe reaction is concentrated in vacuo
  3. customthe residue partitioned between ethyl acetate (50 mL) and water (50 mL)
  4. extractionThe aqueous layer is extracted twice with ethyl acetate (50 mL)
  5. dry with materialThe combined organic phases are dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2 v/v)
  9. customevaporated

出典と根拠

ORDレコード
ord-ab5292075f4e4004b11a47f8526311d0
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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