Tetrahydrofuran → (6-Chloropyridin-3-yl)methanol

HRID 249483ノート

反応式

HRID 249483 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][N:3]=1.[BH4-].[Na+].C1COCC1>CO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 4311764Sodium borohydride

生成物 1

HCID 177161(6-Chloropyridin-3-yl)methanol収率 91.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of 3.0 g (0.0175 mole) of methyl 6-chloronicotinate, 2.0 g of sodium borohydride and 60 ml of THF on reflux, 8.0 ml of MeOH was added with stirring over a period of 1 hour. After completion of the dropwise addition, the mixture was further refluxed for 30 minutes and when cold, the solvent was distilled off. The residue was diluted with 30 ml of water, saturated with NaCl and extracted with CH2Cl2 (20 ml×3). The CH2Cl2 layer was dried over MgSO4 and the CH2Cl2 was distilled off to give 2.3 g of 6-chloro-3-pyridylmethanol as a yellow oil. When left standing at room temperature, this product was thoroughly crystallized.

後処理

  1. temperatureon reflux
  2. additionAfter completion of the dropwise addition
  3. temperaturethe mixture was further refluxed for 30 minutes
  4. distillationwhen cold, the solvent was distilled off
  5. additionThe residue was diluted with 30 ml of water, saturated with NaCl
  6. extractionextracted with CH2Cl2 (20 ml×3)
  7. dry with materialThe CH2Cl2 layer was dried over MgSO4
  8. distillationthe CH2Cl2 was distilled off

出典と根拠

ORDレコード
ord-466a1d9719e74887838f13a3dfbf97b8
出典データセット
uspto-grants-1993_05
特許番号
US05214152

反応ノート

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