Tetrahydrofuran → {(S)-6-[(R)-4-Formyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422627Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:30])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH:28]=C)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[O:31]1CCCC1>O=[Os](=O)(=O)=O.O>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH:28]=[O:31])[C:20]([C:24]([F:26])([F:27])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

NaIO4 (1.80 g) and OsO4 (4% in water, 50 μL) are added to a mixture of {(S)-6-[(R)-5-trifluoromethyl-4-vinyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (1.25 g), tetrahydrofuran (16 mL), and water (4 mL) at room temperature. The mixture is stirred at 50° C. overnight. After cooling to room temperature, water is added and the mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate) to give the title compound. LC (method 4): tR=1.19 min; Mass spectrum (ESI+): m/z=421 [M+H]+.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture is extracted with ethyl acetate
extractionThe combined extract
washis washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-414ff3bfdb854f118999f7b128141cff
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927531B2

Reaction notes

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