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Sodium Sulfite → 2-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine 1-oxide

HRID 442726
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HRID 442726 반응식
[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]
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참가 물질

5

반응물 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 543301292-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine

생성물 1

HCID 542239762-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine 1-oxide수율 93.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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:

후처리

  1. stirringThe mixture was stirred for 30 minutes
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

출처 및 근거

ORD 기록
ord-330e2eaa160a465594ed090fd058d7b1
출처 데이터셋
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05891895

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