Potassium Carbonate → Methyl 3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate

HRID 1990005Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CC1C=CC(S(O[C@@H:31]2[CH2:35][CH2:34][O:33][CH2:32]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)CCC>[C:14]1([CH2:13][O:12][C:10]2[CH:9]=[C:4]([CH:3]=[C:2]([O:1][C@H:31]3[CH2:35][CH2:34][O:33][CH2:32]3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (18.8 g, 72.75 mmol), (3R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate (18.5 g, 76.4 mmol) and potassium carbonate (20.08 g, 145.5 mmol) in butyronitrile (250 mL) was heated to 130° C. for 3 hours. The solvent was removed in vacuo and ethyl acetate added. The organics were washed with water (40 mL), 0.5M sodium hydroxide solution (40 mL), brine (40 mL), dried (MgSO4), filtered and the solvent removed in vacuo. The residue was chromatographed on silica, eluting with a gradient of 0-5% methanol in DCM, to give the desired compound as a colourless oil (20.1 g). 1H NMR δ (CDCl3): 2.08-2.26 (m, 2H), 3.78-4.01 (m, 4H), 3.90 (s, 3H), 4.92-4.96 (m, 1H), 5.08 (s, 2H), 6.69 (t, 1H), 7.15 (t, 1H), 7.29 (t, 1H), 7.34-7.44 (m, 5H); m/z 327 (M+H)+

Workup

customThe solvent was removed in vacuo and ethyl acetate
additionadded
washThe organics were washed with water (40 mL), 0.5M sodium hydroxide solution (40 mL), brine (40 mL)
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent removed in vacuo
customThe residue was chromatographed on silica
washeluting with a gradient of 0-5% methanol in DCM

Sources & evidence

ORD record: ord-2a3cb86072c74b2a88dfa47b12b3db27
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642263B2

Reaction notes

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