Sodium borohydride → 1-(3-Methoxy-4-propoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanediol
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:16](=[O:33])[CH2:17][CH2:18][C:19]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)=[O:20])[CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[C:8]=1[O:9][CH2:10][CH2:11][CH3:12].[BH4-].[Na+]>CO.O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]([OH:33])[CH2:17][CH2:18][CH:19]([C:21]2[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=2)[OH:20])[CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[C:8]=1[O:9][CH2:10][CH2:11][CH3:12]Participants
6
Procedure
To a solution of 1-(3-methoxy-4-propoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-butane-1,4-dione (11.53 g, 25 mmole) in 350 mL of methanol and 250 mL of tetrahydrofuran was added dropwise a solution of sodium borohydride (3.076 g, 81.34 mmol) in 140 mL of water. After the addition was completed, the mixture was stirred at room temperature for 3 hours, quenched with water and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and evaporated to provide a foam (11.53 g, 99.24%). 1H NMR (CDCl3): 1.05 (t, 3H), 1.80-1.95 (m, 6H), 3.80-3.98 (m, 12H), 4.1 (t, 2H), 4.72 (m, 2H), 6.6 (s, 2H), 7.15 (s, 1H), 7.35 (s, 1H).
Workup
- additionAfter the addition
- customquenched with water
- extractionextracted with dichloromethane
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-f1ae0b8c544f4c25886aa77aa81c47ee
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05358938
Reaction notes
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