p-Toluenesulfonic acid → Methyl 2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate

HRID 1855043Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:15][CH2:14][C:11]([CH2:16][C:17]([OH:19])=[O:18])([CH2:12][CH2:13]2)[CH2:10][O:9]3)[CH:5]=[CH:6][CH:7]=1.[CH3:20]C1C=CC(S(O)(=O)=O)=CC=1>CO>[OH:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:13][CH2:12][C:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])([CH2:14][CH2:15]2)[CH2:10][O:9]3)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid (910 mg, 3.47 mmol) and p-TsOH (66 mg, 0.347 mmol) in MeOH (10 mL) was stirred at 60° C. for 18 h. The reaction was concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes) to afford the title compound (887 mg, 93% yield) as a clear oil. LCMS, [M+H]+=277.3. 1H NMR (500 MHz, CDCl3) δ 7.13 (t, J=7.9 Hz, 1H), 6.93-6.84 (m, 2H), 6.69-6.63 (m, 1H), 6.13 (s, 1H), 3.94 (s, 2H), 3.67 (s, 3H), 2.18 (s, 2H), 2.06-1.94 (m, 4H), 1.86-1.72 (m, 4H).

Workup

concentrationThe reaction was concentrated in vacuo
customThe crude oil was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes)

Sources & evidence

ORD record: ord-be5d2aed78ea4cceb21e12c356b29531
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962660B2

Reaction notes

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