Pyridine → HCID 86602759, compound

HRID 349716Notes

Reaction equation

[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:6][O:7][CH2:8][C:9]([CH3:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:10][OH:11].N1C=CC=CC=1.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(Cl)Cl>[CH3:44][C:34]1[CH:39]=[CH:38][C:37]([S:40]([O:11][CH2:10][C:9]([CH3:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][O:7][CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:26])([F:27])[F:1])[CH:21]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:19]=2)(=[O:42])=[O:41])=[CH:36][CH:35]=1

Participants

Conditions

Temperature: -20 °C

Procedure

3-(3,5-bis(trifluoromethyl)benzyloxy)-2-methyl-2-phenylpropan-1-ol (1.72 g, 4.39 mmol) was mixed with pyridine (1.39 g, 17.6 mmol) in anhydrous methylene chloride (20 ml) and cooled to −20° C. Solid p-toluenesulfonyl chloride (3.35 g, 17.6 mmol) was added in one portion and the mixture was warmed up naturally to room temperature and stirred overnight. The mixture was then loaded directly onto silica column and eluted with 5% ethyl aceta in hexanes. 1.89 g (79%) of the desired product was obtained. 1H NMR (500 MHz, CDCl3) δ: 1.37 (s, 3 H) 2.38 (s, 3 H) 3.66 (d, J=2.75 Hz, 2 H) 4.21 (d, J=9.46 Hz, 1 H) 4.27 (d, J=9.46 Hz, 1 H) 4.52 (s, 2 H) 7.27 (m, 5 H) 7.35 (d, J=8.24 Hz, 2 H) 7.62 (s, 2 H) 7.70 (s, 1 H) 7.80 (d, J=8.24 Hz, 2 H).

Workup

temperaturethe mixture was warmed up naturally to room temperature
washeluted with 5% ethyl

Sources & evidence

ORD record: ord-926bacca6f25465d8efc3c87c351e852
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179926B2

Reaction notes

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