Ethanol → 3-Chloro-5-(hydroxymethyl)benzamide

HRID 1260866ノート

反応式

HRID 1260866 の反応式
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[C:7](OC)=[O:8])=[O:3].C(O)C.[BH4-].[Li+]>O1CCCC1>[Cl:14][C:12]1[CH:13]=[C:4]([CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=1)[C:2]([NH2:1])=[O:3]

参加物

5

反応物 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 58963003Methyl 3-carbamoyl-5-chlorobenzoate

生成物 1

HCID 589629763-Chloro-5-(hydroxymethyl)benzamide収率 49.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

(Step 1) To a mixed solution of methyl 3-(aminocarbonyl)-5-chlorobenzoate (2.2 g) in tetrahydrofuran:ethanol=10:1 (33 ml) was added lithium tetrahydroborate (0.34 g) at room temperature. After stirring at 60° C. for 2 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=5:1) to give 3-chloro-5-(hydroxymethyl)benzamide (0.95 g).

後処理

  1. customthe reaction solution was quenched with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionthe obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=5:1)

出典と根拠

ORDレコード
ord-15baf875d4e64000b1190902858adec3
出典データセット
uspto-grants-2013_06
特許番号
US08470859B2

反応ノート

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