3,4-dihydro-2H-pyran → HCID 21202089, compound

HRID 1978897Notes

Reaction equation

HRID 1978897 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][OH:12].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>ClCCl.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][O:12][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][O:13]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 104896782-(2-BROMO-5-METHOXYPHENYL)ETHANOL

Product 1

HCID 21202089HCID 21202089, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-(2-bromo-5-methoxyphenyl)ethanol (1.5 g, 6.5 mmol) and dihydropyran (13.0 mmol) in dry dichloromethane (30 ml) was added camphor sulfonic acid (0.3 mmol) under nitrogen at 0° C. for 1 hour. The reaction mixture was quenched with saturated sodium bicarbonate solution, and extracted with dichloromethane. The organic extracts were washed with brine, dried over magnesium sulfate, and concentrated to give a crude product. This was purified by silica-gel column chromatography eluted with a mixed solvent of hexane and ethyl acetate (20:1) to give the title compound (2.05 g, quantitative). 1H-NMR (CDCl3): 7.40 (d, J=8.8 Hz, 1H), 6.86 (d, J=2.9 Hz, 1H), 6.65 (dd, J=8.8, 2.9 Hz, 1H), 4.63-4.60 (m, 1H), 3.99-3.90 (m, 1H), 3.82-3.74 (m, 1H), 3.78 (s, 3H), 3.68-3.59 (m, 1H), 3.50-3.45 (m, 1H), 3.02 (t, J=7.0 Hz, 2H), 1.83-1.52 (m, 6H).

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a crude product
  7. customThis was purified by silica-gel column chromatography
  8. washeluted with a mixed solvent of hexane and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-be8c4d6221be418281b9db3e868ff95a
Source dataset
uspto-grants-2001_05
Patent number
US06239147B1

Reaction notes

Loading…