Sodium borohydride → 4-(2-(2-Hydroxymethylbenzoyl)aminoethylthio]pyridine

HRID 6151ノート

反応式

HRID 6151 の反応式
[C:1]1(=[O:20])[N:5]([CH2:6][CH2:7][S:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[C:3]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:2]12.[BH4-].[Na+].C(O)C.C(OCC)(=O)C>C(O)C>[OH:20][CH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:5][CH2:6][CH2:7][S:8][C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)=[O:15]

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 190792564-(2-Phthalimidoethylthio)pyridineHCID 21584252Ethanol ethylacetate

生成物 1

HCID 190791794-(2-(2-Hydroxymethylbenzoyl)aminoethylthio]pyridine収率 77.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2.84 g (10.0 mmol) of 4-(2-phthalimidoethylthio)pyridine in 150 ml of ethanol, 3.78 g (100 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 3 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10 to give 2.24 g of the desired compound (77.8% yield, colorless crystals), mp. 132°-133° C.

後処理

  1. distillationThe solvent was distilled off
  2. additionsaturated saline was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent

出典と根拠

ORDレコード
ord-b2748f3faf0e4cadb94edae14f08f39f
出典データセット
uspto-grants-1993_09
特許番号
US05246948

反応ノート

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