Triethylamine → 4-hydroxy-2-isopentyl-2-phenyl-5-[(2-phenylphenyl)methylsulfanyl]-3H-pyran-6-one

HRID 357872Notes

Reaction equation

[OH:1][C:2]1[CH2:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[O:5][C:4](=[O:19])[CH:3]=1.C1(C)C=CC([S:26](=S)(O)=O)=CC=1.[CH3:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(OCC)C.C(O)C>[C:32]1([CH2:31][S:26][C:3]2[C:4](=[O:19])[O:5][C:6]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:7][C:2]=2[OH:1])[C:33]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:34][CH:35]=[CH:36][CH:37]=1

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-(3-methylbutyl)-2H-pyran-2-one (0.250 g, 0.96 mmol), (2-methylbiphenyl)-p-toluenethiosulfonate (0.439 g, 1.24 mmol), Et3N (0.17 mL, 1.24 mmol), absolute ethanol (3.0 mL), NaHCO3 (0.5 g). 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 (0.33 g, m.p. 49°-51° C.). 1H NMR (400 MHz, DMSO-d6) δ 7.425-7.153 (m, 13 H), 7.74 (dd, 1 H, J=1 Hz, J=7 Hz), 3.480 (dd, 2 H, J=12 Hz, J=17 Hz), 3.149 (dd, 2 H, J=17 Hz, J=22 Hz), 1.921-1.821 (m, 2 H), 1.402-1.336 (m, 1 H), 1.161-1.071 (m, 1 H), 0.847-0.707 (m, 7 H).

Workup

washwashed with H2O
customThe solvent was then removed in vacuo

Sources & evidence

ORD record: ord-5e6a0acf55fb4eb889aa326336cb04c9
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840751

Reaction notes

Loading…