Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 90409618, compound

HRID 1855073Notes

Reaction equation

HRID 1855073 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:15]23[CH2:22][CH2:21][C:18]([CH2:23][CH2:24][O:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([CH2:19][CH2:20]2)[CH2:17][O:16]3)[CH:5]=[C:6]([O:8]C2CCCCO2)[CH:7]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[F:1][C:2]1[CH:3]=[C:4]([C:15]23[CH2:20][CH2:19][C:18]([CH2:23][CH2:24][O:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([CH2:21][CH2:22]2)[CH2:17][O:16]3)[CH:5]=[C:6]([OH:8])[CH:7]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 90408389HCID 90408389, compound

Product 1

HCID 90409618HCID 90409618, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl 2-(2-(1-(3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate (400 mg, 0.861 mmol) and PPTS (65 mg, 0.258 mmol) in MeOH (10 mL) was stirred at 50° C. for 3 h. The reaction was cooled to rt, then concentrated in vacuo. The residual crude oil was purified by flash chromatography (SiO2) using a gradient from 0% to 30% EtOAc/hexane (10 min) to give the title compound (292 mg, 0.768 mmol, 89% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ: 6.71-6.66 (m, 1H), 6.66-6.61 (m, 1H), 6.42 (d, J=10.2 Hz, 1H), 5.96 (s, 1H), 3.96 (s, 2H), 3.88 (s, 2H), 3.58 (t, J=6.9 Hz, 2H), 2.04-1.92 (m, 4H), 1.80-1.70 (m, 4H), 1.57-1.49 (m, 11H); 19F NMR (471 MHz, CDCl3) δ: −112.25 (s, 1F).

Workup

  1. temperatureThe reaction was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe residual crude oil was purified by flash chromatography (SiO2)
  4. customfrom 0% to 30% EtOAc/hexane (10 min)

Sources & evidence

ORD record
ord-4b384973a5c24d82beaa09202f1a51ef
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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