Hydrochloric Acid → 6-chloro-8-[(3-fluorophenyl)ethynyl]-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 855001Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]([C:26]([F:29])([F:28])[F:27])[O:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=2[C:17]#[C:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)=[O:5])C.C1COCC1.CCO.O.O[Li].O.Cl>O>[Cl:16][C:12]1[CH:13]=[C:14]2[C:9](=[C:10]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH:11]=1)[O:8][CH:7]([C:26]([F:28])([F:29])[F:27])[C:6]([C:4]([OH:5])=[O:3])=[CH:15]2

Participants

Conditions

Temperature: 60 °C

Procedure

To 0.440 g (1.036 mmole) of ethyl-6-Chloro-8-[(3-fluorophenyl)ethynyl]-2-(trifluoromethyl)-2H-chromene-3-carboxylate was added 5.2 mL of a solvent mixture of THF/EtOH/H2O (7:2:1) followed by 65 mg (1.55 mmole) of LiOH—H2O. The mixture was stirred at 60° C. for two hours. The mixture was concd, diluted with water and acidified with 0.5N HCl. The crude material was purified using reverse phase chromatography to afford 0.387 g (94%) of a yellow crystalline solid: 1H NMR (CDCl3/400 MHz) 5.79 (q, 1H, J=6.4 Hz), 7.04-7.09 (m, 1H), 7.21-7.23 (m, 2H), 7.31-7.33 (m, 2H), 7.50 (d, 1H, J=2.4 Hz), 7.84 (s, 1H); MS (ES+) 397 (M+1, 100); HRMS (ES−) m/z calcd for (C19H9O3ClF4) 395.0093, found 395.0092.

Workup

customThe crude material was purified

Sources & evidence

ORD record: ord-9996d39540074113a798002bdd559dbe
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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