Water → (4s)-6-Methyl-4-phenylchroman-2-one
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][C@H:5]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1C=C(Cl)C=C(C(OO)=[O:26])C=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[O:26][C:7](=[O:11])[CH2:6][C@H:5]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
Procedure
5-Methyl-3-(S)-phenyl-indan-1-one (400 mg, 1.8 mmol) and mCPBA (98%, 485 mg, 2.8 mmol) were suspended in dry CH2Cl2 (6 ml) at 0° C. followed by TsOH:H2O (20 mg). The reaction was kept at 4° C. for 48 h. The mixture was diluted with 10 ml of CH2Cl2 and washed with 2×10 ml of saturated Na2SO3, saturated NaHCO3 and brine. Flash chromatography eluting with ethyl acetate:pentane 10:90 gave 390 mg (90%) of the title compound. Rf 0.83 (ethyl acetate:pentane 20:80) (ChiralCel OD-H) 0.5 mL/min of hexane/isopropanol 95/5 (S)-isomer 15.18 min, (R)-isomer 17.42 min, 89% ee. IR (neat cm−1): 2900, 2360, 1769, 1495, 1208, 1145. 1H NMR δ: 2.28 (s, 3H), 3.05 (m, 1H), 4.32 (t, J=6.8Hz, 1H), 6.98 (s, 1H), 7.04 (d, J=8.4Hz, 1H), 7.11 (dd, J=2.0, 8.4Hz, 1H), 7.18 (d, J=8.4Hz, 1H), 7.19 (s, 1H), 7.33 (m, 3H) 13C NMR δ: 20.7, 37.1, 40.7, 116.8, 125.3, 127.5, 127.6, 128.6, 129.1, 129.3, 134.3, 140.5, 149.6, 167.8. MS (EI 70 eV) m/z (rel. intensity): 238 (55) [M+], 220 (57), 195 (100), 181(10), 165 (12), 152 (9).
Workup
- washwashed with 2×10 ml of saturated Na2SO3, saturated NaHCO3 and brine
- washFlash chromatography eluting with ethyl acetate:pentane 10:90
Sources & evidence
- ORD record
- ord-285a598de22041ea9a3b934cdfd6b22c
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06689916B2
Reaction notes
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