4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde → 6-(1-Hydroxyethyl)-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH:16]=[O:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]1=[O:18].[CH3:19][Mg]Br>O1CCCC1>[OH:17][CH:16]([C:13]1[CH:14]=[CH:15][C:10]2[O:9][CH2:8][C:7](=[O:18])[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:11]=2[CH:12]=1)[CH3:19]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
The solution of 1.0 g of 4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde and 30 ml of tetrahydrofuran is cooled to 0° C. and admixed dropwise with 1.4 ml of methylmagnesium bromide (35% in THF). The reaction mixture is stirred at 0° C. for a further 15 minutes, subsequently quenched with saturated ammonium chloride solution (50 ml) and extracted with tert-butyl methyl ether (2×50 ml). The organic phases are washed successively with ice-water (50 ml) and brine (50 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.16 (3:1 EtOAc-heptane); Rt=2.96.
Workup
- customsubsequently quenched with saturated ammonium chloride solution (50 ml)
- extractionextracted with tert-butyl methyl ether (2×50 ml)
- washThe organic phases are washed successively with ice-water (50 ml) and brine (50 ml)
- dry with materialdried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-d6fdbcfdf18b48f584d67d6d1b4abf72
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790715B2
Reaction notes
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