Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → methyl 3-(3,6-dihydro-2H-pyran-4-yl)-4-hydroxybenzoate

HRID 1662433Notes

Reaction equation

[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[O:17]C2CCCCO2)[C:10]([O:12][CH3:13])=[O:11])[CH2:3][CH2:2]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[O:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[OH:17])[C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred mixture of 66.46C (0.73 g, 2.30 mmol) in MeOH (10 mL) was added PPTS (58.8 mg, 0.234 mmol). The mixture was heated to 45° C. and monitored with TLC and LCMS. After 19 hours, the organic solvent was removed under reduced pressure and the residue was purified on silica gel (0-25% EtOAc in hexanes) to afford 66.46D (361 mg, 67% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.87 (2H, td, J=8.7, 2.2 Hz), 6.95 (1H, d, J=8.6 Hz), 6.00 (1H, m), 5.94 (1H, s), 4.34 (2H, q, J=2.7 Hz), 3.97 (2H, t, J=5.5 Hz), 3.89 (3H, s), 2.47 (2H, ddd, J=9.8, 5.5, 2.7 Hz).

Workup

customthe organic solvent was removed under reduced pressure
customthe residue was purified on silica gel (0-25% EtOAc in hexanes)

Sources & evidence

ORD record: ord-259ad09ce9354397b8ca167fb94ed886
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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