p-Toluenesulfonic acid → HCID 11119203, compound

HRID 1531766Notes

Reaction equation

HRID 1531766 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][OH:9])[N:3]=1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Br:1][C:2]1[N:3]=[C:4]([CH2:8][O:9][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][O:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 11119203HCID 11119203, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromopyridine-6-methanol (prepared as described in Tetrahedron Lett., 1996, 50, 2537) (5 g, 26.5 mmol) was added to a solution of dihydropyran (2.65 ml, 29.2 mmol), and p-toluenesulfonic acid (506 mg, 2.7 mmol) in dichloromethane (150 ml) at room temperature under nitrogen. After 24 h, the mixture was washed with sodium carbonate solution (×1) and water (×1), dried (MgSO4), evaporated in vacuo and the residue flash chromatographed on silica gel, eluting with 10% ethyl acetate/hexane to give the title-compound (6.04 g, 84%), 1H NMR (250 MHz, CDCl3) δ 1.5-1.9 (6H, m, 3 of CH2), 3.56 (1H, m, CH2O), 3.88 (1H, m, CH2O), 4.62 (1H, d, J=14.2 Hz, CH2O), 4.76 (1H, t, J=3.4 Hz, CHO), 4.93 (1H, d, J=14.6 Hz, CH2O), 7.37 (1H, d, J=7.6 Hz, Ar—H), 7.46 (1H, d, J=6.6 Hz, Ar—H), 7.56 (1H, t, J=7.6 Hz, Ar—H); MS (ES30) m/e 272 [MH]+.

Workup

  1. washthe mixture was washed with sodium carbonate solution (×1) and water (×1)
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customthe residue flash chromatographed on silica gel
  5. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9a2e206d91cd4d52b66921340b99f965
Source dataset
uspto-grants-2001_03
Patent number
US06200975B1

Reaction notes

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