p-Toluenesulfonic acid monohydrate → HCID 57475766, compound

HRID 2060762Notes

Reaction equation

HRID 2060762 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2(O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:13][CH2:12][O:11][CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 189962824-(3-Bromophenyl)-tetrahydro-2H-pyran-4-ol

Product 1

HCID 57475766HCID 57475766, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(3-bromophenyl)tetrahydro-2H-pyran-4-ol (11.17 g, 41.3 mmol) and p-toluenesulfonic acid monohydrate (0.797 g, 4.13 mmol) in toluene (100 mL) is heated to reflux for 30 minutes using a Dean-Stark trap to remove water. The reaction is diluted with water and 5 N NaOH and extracted with EtOAc. The organic layer is dried over Na2SO4 and the solvent is removed under reduced pressure to afford a residue that is purified on silica gel chromatography eluting with a linear gradient of 5% to 100% EtOAc in hexanes to give the title compound (8.85 g, 90%). 1H NMR (400 MHz, CDCl3) δ 2.45-2.50 (m, 2H), 3.92 (t, 2H, J=5.71 Hz), 4.31 (q, 2H, J=3.07 Hz, J=5.71 Hz), 6.12-6.14 (m, 1H), 7.19 (t, 1H, J=7.91 Hz), 7.28-7.32 (m, 1H), 7.36-7.39 (m, 1H), 7.51 (t, 1H, J=1.76 Hz).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 30 minutes
  3. customto remove water
  4. additionThe reaction is diluted with water and 5 N NaOH
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer is dried over Na2SO4
  7. customthe solvent is removed under reduced pressure
  8. customto afford a residue that
  9. customis purified on silica gel chromatography
  10. washeluting with a linear gradient of 5% to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-8191954d7e094399a95d88a1138c9876
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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