Hydrochloric Acid → HCID 58934444, compound

HRID 854998Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]([C:21]([F:24])([F:23])[F:22])[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][CH2:19][CH3:20])=[O:5])C.C1COCC1.CCO.O.O[Li].O.Cl>O>[C:17]([C:10]1[CH:11]=[C:12]([Cl:16])[CH:13]=[C:14]2[C:9]=1[O:8][CH:7]([C:21]([F:22])([F:23])[F:24])[C:6]([C:4]([OH:5])=[O:3])=[CH:15]2)#[C:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

To 0.768 g (2.14 mmole) of ethyl-8-but-1-ynyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3- carboxylate was added 11 mL of a solvent mixture of THF/EtOH/H2O (7:2: 1) followed by 135 mg (3.22 mmole) of LiOH—H2O. The mixture was stirred at 60° C. for two hours. The mixture was concd, treated with water, and acidified with 0.5N HCl. The crude solid was purified by reverse phase chromatography to afford 0.575 g (81%) of a yellow crystalline solid: 1H NMR (CDCl3/400 MHz) 1.24 (t, 3H, J=7.2 Hz), 2.46 (q, 2H, J=7.6 Hz), 5.74 (q, 1H J=6.8 Hz), 7.16 (d, 1H, J=2.8 Hz), 7.39 (d, 1H, J=2.4 Hz), 7.81 (s, 1H); MS (ES+) 331 (M+1, 100); HRMS (ES−) m/z calcd for (C15H10O3ClF3) 329.0187, found 329.0202.

Workup

customThe crude solid was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-42331f268d214cf582514a3b2dc3d1ac
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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