Sodium Bicarbonate → N-(2-butyl-3-hydroxy-2,3-dihydro-5-benzofuranyl)acetamide

HRID 971078ノート

反応式

HRID 971078 の反応式
Br[CH:2]([CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])=[O:4].C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO>[CH2:16]([CH:2]1[CH:3]([OH:4])[C:5]2[CH:6]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[CH:8]=[CH:9][C:10]=2[O:11]1)[CH2:17][CH2:18][CH3:19]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 9880472N-[3-(2-bromohexanoyl)-4-hydroxyphenyl]acetamide

生成物 1

HCID 9834788N-(2-butyl-3-hydroxy-2,3-dihydro-5-benzofuranyl)acetamide収率 80.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of N-[3-(2-bromohexanoyl)-4-hydroxyphenyl]acetamide [6a] (3.28 g, 10.0 mmol), sodium bicarbonate (0.84 g, 10.0 mmol) and methanol (30 mL) was stirred under reflux conditions for 2 hours. Sodium borohydride (0.76 g, 20.0 mmol) was added in several portions to the mixture at 0-5° C. (ice/water bath). The mixture was stirred for 1 hour at the same temperature. Methanol (20 mL) was evaporated from the mixture and water (100 mL) was added to the residue. The obtained mixture was stirred for 1 hour at 0-5° C. (ice/water bath). The precipitated crystals were filtered and dried under reduced pressure at 50-60° C. to give 2.01 g (80.6% yield from 2 steps) of N-(2-butyl-3-hydroxy-2,3-dihydro-5-benzofuranyl)acetamide [9a] as off-white crystals with mp 134-137° C.

後処理

  1. stirringThe mixture was stirred for 1 hour at the same temperature
  2. customMethanol (20 mL) was evaporated from the mixture and water (100 mL)
  3. additionwas added to the residue
  4. stirringThe obtained mixture was stirred for 1 hour at 0-5° C. (ice/water bath)
  5. filtrationThe precipitated crystals were filtered
  6. customdried under reduced pressure at 50-60° C.

出典と根拠

ORDレコード
ord-aa4cadc8f43248338d2bf86c432aab28
出典データセット
uspto-grants-2007_12
特許番号
US07312345B2

反応ノート

読み込み中…