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

HRID 971078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971078
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 9834788N-(2-butyl-3-hydroxy-2,3-dihydro-5-benzofuranyl)acetamideAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-aa4cadc8f43248338d2bf86c432aab28
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312345B2

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