Sodium Bicarbonate → N-(2-butyl-3-hydroxy-2,3-dihydro-5-benzofuranyl)acetamide
Reaction equation
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]Participants
Procedure
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.
Workup
- stirringThe mixture was stirred for 1 hour at the same temperature
- customMethanol (20 mL) was evaporated from the mixture and water (100 mL)
- additionwas added to the residue
- stirringThe obtained mixture was stirred for 1 hour at 0-5° C. (ice/water bath)
- filtrationThe precipitated crystals were filtered
- customdried under reduced pressure at 50-60° C.
Sources & evidence
- ORD record
- ord-aa4cadc8f43248338d2bf86c432aab28
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312345B2
Reaction notes
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