Triethylamine → 5,6-Dihydro-4-hydroxy-3-[(2,5-dimethylphenyl)methylthio]-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

HRID 357871Notes

Reaction equation

[OH:1][C:2]1[CH2:7][C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:22])[CH:3]=1.CC1C=CC(C)=CC=1[CH2:26][C:27]1C=[C:31]([S:33](=S)([O-])=O)[CH:30]=[CH:29][C:28]=1[CH3:37].CCN([CH2:48][CH3:49])CC.C([O-])(O)=O.[Na+]>C(OCC)C.C(O)C>[OH:1][C:2]1[CH2:7][C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:22])[C:3]=1[S:33][CH2:31][C:30]1[CH:29]=[C:28]([CH3:37])[CH:27]=[CH:26][C:48]=1[CH3:49]

Participants

Conditions

Temperature: 40 °C

Procedure

The title compound was prepared as described in General Method 7 using the following: 5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (0.250 g, 0.850 mmol), 2,5-dimethylbenzyl-p-toluenethiosulfonate (0.312 g, 1.02 mmol), Et3N (0.230 mL, 1.60 mmol), NaHCO3 (0.071 g, 0.85 mmol), absolute ethanol (3.0 mL). The mixture was heated to 40° C. for 16 h then diluted with diethyl ether (100 mL), and washed with H2O. The solvent was then removed in vacuo and the residue submitted to column chromatography (SiO2, 100% CH2Cl2 to 2% methanol in CH2Cl2) to provide a solid (0.116 g, m.p. 54°-56° C.) which was dried in vacuo. 1H NMR (400 MHz, DMSO-d6) δ 11.498 (bs, 1 H), 7.405-7.380 (m, 4 H), 7.327-7.285 (m, 1 H), 7.258-7.221 (m, 2 H), 7.168-7.128 (m, 1 H), 7.090 (d, 2 H, J=7.5 Hz), 6.970 (d, 1 H, J=8 Hz), 6.890 (d, 1 H, J=8 Hz), 6.821 (s, 1 H), 3.600 (d, 1 H , J=11 Hz), 3.505 (d, 1 H, J=11 Hz), 3.250 (d, 1 H, J=17 Hz), 3.176 (d, 1 H, J=17), 2.619-2.564 (m, 1 H), 2.235-2.168 (m, 9 H).

Workup

washwashed with H2O
customThe solvent was then removed in vacuo

Sources & evidence

ORD record: ord-ca4917548290472c975ab7471d000bb2
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840751

Reaction notes

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