C=C1C=[CH:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4]C1.CS(N)(=O)=O.S(=O)(O)[O-].[Na+].[OH2:23].[C:24]([OH:28])([CH3:27])([CH3:26])[CH3:25]>[Os](=O)(=O)(=O)=O>[OH:23][CH2:25][C:24]1([OH:28])[CH:27]=[CH:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:26]1
160 mg (1 mmol) of 3-methylene-2,3-dihydro-1-benzoxepin, prepared according to example 23, are added to a mixture of 250 mg (1 mmol) of osmium tetroxide and 95 mg (1 mmol) of methanesulfonamide dissolved in 10 ml of a 1/1 water/tert-butanol mixture. After 12 hours at ambient temperature, 1.5 g of sodium bisulfite are introduced and the medium is stirred for one hour. Extraction with dichloromethane and then purification (purification is carried out by chromatography on silica gel (dichloromethane/methanol: 95/5)) provides 192 mg (95%) of 3-(hydroxymethyl)-2,3-dihydro-1-benzoxepin-3-ol in the form of a white solid; 1H NMR (300 MHz, CDCl3): 7.28–7.18 (m, 2H), 7.08–6.9 (m, 2H), 6.41 (d, J=12 Hz, 1H), 5.85 (d, J=11.2 Hz, 1H), 4.14 (d, J=11.7 Hz, 1H), 4.14 (d, J=11.7 Hz, 1H), 3.72–3.62 (m, 2H), 2.69 (broad s, 1H, OH), 2.28 (broad s, 1H, OH).
Wird geladen…
