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

HRID 971078노트

반응식

HRID 971078 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-aa4cadc8f43248338d2bf86c432aab28
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312345B2

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