Diisopropylethylamine → 3-Trifluoromethylbenzenesulfonic acid 3-benzyloxy-5-methylphenyl ester

HRID 482109Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:16])[CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[F:26][C:27]([F:39])([F:38])[C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1>C(Cl)Cl.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:16][S:34]([C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([C:27]([F:26])([F:38])[F:39])[CH:29]=2)(=[O:36])=[O:35])[CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-benzyloxy-5-methylphenol (400 mg, 2.0 mmol), as prepared in step a of Example 3, in methylene chloride (10 mL) at 0° C. was treated with N,N-diisopropylethylamine (0.4 mL) and 3-trifluoromethylbenzenesulfonyl chloride (489 mg, 2.0 mmol). The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 2 h. The reaction mixture was diluted with methylene chloride (200 ml,) and water (50 mL). The organic extract was washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a colorless liquid (710 mg, 85%). 1H-NMR (300 MHz, CDCl3) δ 2.25 (s, 3H), 4.94 (s, 2H), 6.41 (s, 2H), 6.72 (s, 1H), 7.37 (m, 5H), 7.68 (t, 1H), 7.91 (d, 1H), 8.03 (d, 1H), 8.09 (s, 1H).

Workup

extractionThe organic extract
washwas washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (1:1 hexane:methylene chloride)

Sources & evidence

ORD record: ord-b191d134fb3f4501b303905265e83429
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05792769

Reaction notes

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