3,4-dihydro-2H-pyran → 4-Bromo-2-t-butyl-1-(2-tetrahydropyranoxy)benzene

HRID 1940227Notes

Reaction equation

HRID 1940227 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 970684-Bromo-2-tert-butylphenol2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 158188564-Bromo-2-t-butyl-1-(2-tetrahydropyranoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 18.92 g (82.6 mmol) of 4-bromo-2-t-butylphenol (Compound E) in 110 ml of dichloromethane was added dropwise 10.42 g (11.3 ml, 123.9 mmol) of 3,4-dihydro-2H-pyran. To this clear, colorless solution was added 1.86 g (7.4 mmol) of pyridinium p-toluenesulfonate. The resulting mixture was stirred at room temperature under a blanket of argon for 26.5 hours, partitioned between 250 ml of water and 400 ml of hexane, and the layers were separated. The organic phase was washed with 2×250 ml-portions of water and 150 ml of brine solution, dried over MgSO4, filtered and concentrated in vacuo to a yellow oil. Purification by flash chromatography (silica, 5% ethyl acetate in hexane) yielded the title compound as a light yellow, crystalline solid. PMR (CDCl3): d 1.39 (9H, s), 1.6-2.1 (6H, m), 3.6-3.7 (1H, m), 3.8-3.9 (1H, m), 5.43 (1H, t, J=2.7 Hz), 7.06 (1H, d, J=8.8 Hz), 7.24 (1H, dd, J=8.8, 2.7 Hz), 7.36 (1H, d, J=2.7 Hz).

Workup

  1. custompartitioned between 250 ml of water and 400 ml of hexane
  2. customthe layers were separated
  3. washThe organic phase was washed with 2×250 ml-portions of water and 150 ml of brine solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a yellow oil
  7. customPurification by flash chromatography (silica, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-052efa6210a14717b5a67496e60dcbe2
Source dataset
uspto-grants-1997_12
Patent number
US05698700

Reaction notes

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