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Ethyl Acetate → {6-[(2-Fluorophenyl)methoxy]pyridin-3-yl}methanol

HRID 1794081
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HRID 1794081 반응식
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][N:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][OH:11])=[CH:8][N:7]=1
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참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 222200456-[(2-Fluorophenyl)methoxy]pyridine-3-carboxylic acid

생성물 1

HCID 22220075{6-[(2-Fluorophenyl)methoxy]pyridin-3-yl}methanol수율 75%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

to a stirred solution of 6-(2-fluorobenzyloxy)nicotinic acid (0.89 g) in THF (10 ml) at 0° C. under Ar was added dropwise a solution of lithium aluminium hydride (1.0 M, 5.5 ml). The mixture was warmed to room temperature and stirred for 2 h. Saturated potassium sodium tartrate solution (1 ml) was added to the mixture followed by ethyl acetate (10 ml). The mixture was stirred for 30 min, filtered and concentrated in vacuo to give the product as a clear oil (0.63 g) which was used without further purification; δH (400 MHz, CDCl3) 8.14 (1H, d, J 1.5 Hz), 7.63 (1H, dd, J 8.5, 2.5 Hz), 7.49 (1H, dt, J 7.5, 1 Hz), 7.29 (1H, m), 7.13 (1H, dt, J 7.5, 1 Hz), 7.02 (1H, dt, J 10, 1 Hz), 6.81 (1H, d, J 8 Hz), 5.45 (2H, s) and 4.63 (2H, s); LC 73%, 2.24 min.

후처리

  1. stirringThe mixture was stirred for 30 min
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d39c6df19fb040bc8ffdbe3a44beb477
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07022707B2

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