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Methyl Ethyl Ketone → [5-(3-Fluoro-benzyloxy)-pyridin-2-yl]-methanol

HRID 433212
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HRID 433212 반응식
Cl.[OH:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[N:9][CH:8]=1
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참가 물질

6

반응물 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 187584236-(Hydroxymethyl)pyridin-3-ol hydrochloride

생성물 1

HCID 11148991[5-(3-Fluoro-benzyloxy)-pyridin-2-yl]-methanol수율 67.5%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
80 °C

실험 절차

A mixture of 6-hydroxymethyl-pyridin-3-ol hydrochloride (1:1) (6.29 g, 38.9 mmol), 3-fluorobenzyl bromide (8.1 g, 42.8 mmol), potassium carbonate (10.76 g, 77.9 mmol) and 2-butanone (200 ml) was heated to 80° C. for 5 h. After cooling, water was added, and the mixture extracted with ethyl acetate. After drying of the organic layer with MgSO4, filtration and evaporation, the residue was purified by chromatography (SiO2, CH2Cl2—MeOH 95:5) to give the title compound as a brown solid (6.12 g, 67%). MS: m/e=234.3 (M+H+).

후처리

  1. temperatureAfter cooling
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialAfter drying of the organic layer with MgSO4, filtration and evaporation
  4. customthe residue was purified by chromatography (SiO2, CH2Cl2—MeOH 95:5)

출처 및 근거

ORD 기록
ord-212f6b30f78c462f88c2cd380fcb40f3
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06667327B2

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