Sodium Sulfite → 2-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine 1-oxide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH:5]([C:7]1[C:12]([O:13][CH2:14][O:15][CH3:16])=[CH:11][CH:10]=[CH:9][N:8]=1)[OH:6].ClC1C=CC=C(C(OO)=[O:28])C=1.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH:5]([C:7]1[C:12]([O:13][CH2:14][O:15][CH3:16])=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:28])[OH:6]Participants
5
Procedure
A mixture of 2-(3-bromo-α-hydroxybenzyl)-3-methoxymethoxy pyridine (4.65 g), 70% m-chloro-perbenzoic acid (7.10 g) and tetrahydrofuran (200 mL) was stirred overnight at room temperature, to which was poured an aqueous solution of sodium sulfite. The mixture was stirred for 30 minutes, and then subjected to extraction with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate) and then concentrated. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromo-α-hydroxybenzyl)-3-methoxymethoxypyridine 1-oxide (4.58 g). Spectrum data of the product are shown below:
Workup
- stirringThe mixture was stirred for 30 minutes
- extractionsubjected to extraction with ethyl acetate
- washThe extract was washed with water
- dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
- concentrationconcentrated
- customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)
Sources & evidence
- ORD record
- ord-330e2eaa160a465594ed090fd058d7b1
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05891895
Reaction notes
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