Hydrochloric Acid → HCID 57864412, compound

HRID 1672657Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+].Cl>C1COCC1.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)=[C:6]([CH2:7][OH:8])[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3.50 g (10.3 mmol) of 5-fluoro-2-[3-(4-trifluoromethylphenyl)prop-2-ynyloxy]benzoic acid are suspended in 10 ml of THF, 1.04 g (10.3 mmol) of N-methylmorpholine are added, the mixture cooled to 0° C., and 1.12 g (10.3 mmol) of ethyl chloroformate are added. The mixture is warmed to room temperature and stirred for 30 min. 1.17 g (31.0 mmol) of sodium borohydride are added to this solution, and the mixture is stirred at room temperature for 5 h. Then methanol is added until gas evolution has subsided, and subsequently 1 N hydrochloric acid is used to acidify. The solvent is distilled out in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried over sodium sulfate, and the solvent is distilled out in vacuo. 4.62 g (8.69 mmol, 85% of theory) of the title compound are isolated.

Workup

temperatureThe mixture is warmed to room temperature
stirringthe mixture is stirred at room temperature for 5 h
distillationThe solvent is distilled out in vacuo
washThe organic phase is washed with saturated sodium chloride solution
dry with materialdried over sodium sulfate
distillationthe solvent is distilled out in vacuo

Sources & evidence

ORD record: ord-ec7ed8702966488fbdd1da72fd211d1c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998988B2

Reaction notes

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