Water → 7-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

HRID 2424959

Reaction equation

O[C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[N:17][OH:18])[C:13]([F:16])([F:15])[F:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O>C1COCC1>[CH2:8]([C:7]1[C:2]2[O:18][N:17]=[C:12]([C:13]([F:14])([F:15])[F:16])[C:3]=2[CH:4]=[CH:5][C:6]=1[OH:11])[CH2:9][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(2,4-Dihydroxy-3-propylphenyl)-2,2,2-trifluoroethanone oxime (prepared by the method described in WO 97/28137, 4.2 g, 15.96 mmol) and triphenylphosphine (8.82 g, 33.6 mmol) were dissolved in THF (250 mL) and the mixture was cooled to 0° C. A solution of diethyl azodicarboxylate (5.02 mL, 32.0 mmol) in THF (150 mL) was then slowly added over a period of 30 minutes. The reaction mixture was stirred for 1 h at 0° C. After addition of water (500 mL), the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. The solvent was removed in vacuo and the product purified via silica gel flash chromatography (ethyl acetate/hexane (v/v)=1:6). The product was obtained as a white-yellow powder in a yield of 1.96 g (8.0 mmol, 50%). 1H NMR (300 MHz, CDCl3) δ 1.00 (t, 3H), 1.73 (m, 2H), 2.88 (t, 2H), 5.34 (s, 1H), 6.93 (d, 1H), 7.48 (d, 1H).

Workup

extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
customThe solvent was removed in vacuo
customthe product purified via silica gel flash chromatography (ethyl acetate/hexane (v/v)=1:6)
customThe product was obtained as a white-yellow powder in a yield of 1.96 g (8.0 mmol, 50%)

Sources & evidence

ORD record: ord-e154249f3a26420eb9731b55f02b8e65
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964622B2

Linked notes

Loading…