3,4-dihydro-2H-pyran → HCID 18469682, compound

HRID 2228402Notes

Reaction equation

HRID 2228402 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][N:3]=1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1>ClCCl.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][O:10]2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 64212496-Bromo-3-pyridinemethanol

Product 1

HCID 18469682HCID 18469682, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-hydroxymethylpyridine (4 Scheme 27, 7.3 g, 38.8 mmol) and 3,4-dihydro-2H-pyran (3.6 g, 42.7 mmol) in dichloromethane (150 mL) was added p-TsOH (200 mg) and the mixture was stirred for 5 h at room temperature. The reaction mixture was concentrated and purified by column chromatography (1:5 ethyl acetate/hexanes) to give the desired compound as a liquid (10 g, 95%); 1H NMR (300 MHz, CDCl3) δ 1.42-1.81 (6 H), 3.48 (m, 1 H), 3.80 (m, 1 H), 4.43 (m, 1 H), 4.62-4.73 (2 H), 7.42 (m, 1 H), 7.53 (m, 1 H), 8.30 (m, 1 H); 13C NMR (75 MHz, CDCl3) 19.5, 25.5, 30.6, 62.5, 65.8, 98.3, 128.0, 133.5, 138.4, 141.3, 149.7. HRMS (EI) calcd for C11H14BrNO2 271.0208 and 273.0187, found 271.0207 and 273.0171.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography (1:5 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7088c27b8643402aa1e48ac06444dc23
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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