3,4-dihydro-2H-pyran → HCID 90408309, compound

HRID 1855068Notes

Reaction equation

HRID 1855068 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[O:9][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 219046363-Bromo-5-fluorophenol

Product 1

HCID 90408309HCID 90408309, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-5-fluorophenol (1.64 g, 8.59 mmol), 3,4-dihydro-2H-pyran (1.56 mL, 17.2 mmol) and PPTS (0.216 g, 0.859 mmol) in DCM (10 mL) was stirred for 16 h at rt. The reaction was concentrated in vacuo. The residual crude oil was purified by chromatography (SiO2) using a 0% to 20% EtOAc/hexane over 15 min to give the title compound (2.24 g, 8.14 mmol, 95% yield) as a clear oil. 1H NMR (CDCl3) δ: 7.05 (dd, J=2.8, 2.1 Hz, 1H), 6.90 (ddd, J=8.0, 2.2, 1.8 Hz, 1H), 6.77 (dt, J=10.6, 2.2 Hz, 1H), 5.41 (t, J=3.1 Hz, 1H), 3.91-3.81 (m, 1H), 3.72-3.58 (m, 1H), 2.05-1.92 (m, 1H), 1.92-1.82 (m, 2H), 1.81-1.58 (m, 3H); 19F NMR (CDCl3) δ: −110.28 (s); 13C NMR (CDCl3) δ: 164.22 (s), 162.24 (s), 158.78 (d, J=11.8 Hz), 122.41 (d, J=12.5 Hz), 115.88 (d, J=3.3 Hz), 112.33 (s), 112.13 (s), 103.42 (s), 103.22 (s), 96.67 (s), 61.97 (s), 30.05 (s), 25.01 (s), 18.39 (s).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residual crude oil was purified by chromatography (SiO2)
  3. customover 15 min

Sources & evidence

ORD record
ord-9dc65e856128458e85c0fbf6222e460c
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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