2,4-Dihydroxybenzaldehyde → HCID 10537643、化合物

HRID 322948ノート

反応式

HRID 322948 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:14][C:15]1[CH:19]=[CH:18][S:17][CH:16]=1>CN(C)C=O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

参加物

5

反応物 3

HCID 72132,4-DihydroxybenzaldehydeHCID 24758Sodium hydrideHCID 124874623-(Chloromethyl)thiophene

生成物 1

HCID 10537643HCID 10537643、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution of 2,4-dihydroxybenzaldehyde (42.6 g) in dimethylformamide (250 mL) at ambient temperature is treated with sodium hydride (13.5 g; 60% w/v dispersion in mineral oil; 338 mmol), portionwise during 30 minutes. It is then treated with 3-chloromethylthiophene and the reaction mixture is heated at 60° C. for 3 hours. The mixture is concentrated in vacuo and the residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL) and the combined organic extracts are washed with brine (50 mL), dried over magnesium sulphate, filtered and the solvent is removed in vacuo. Flash chromatography on silica gel, using a mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent, gives 2-hydroxy-4-(3-thienylmethoxy)benzaldehyde (11.8 g), in the form of a white solid.

後処理

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL)
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×100 mL)
  4. washthe combined organic extracts are washed with brine (50 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo
  8. additiona mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent

出典と根拠

ORDレコード
ord-c8c18f4c75874b1a910d5d856be4a462
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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