Triethylamine → 3-(Biphenyl-2-ylmethylthio)-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

HRID 357873Notes

Reaction equation

[OH:1][C:2]1[CH2:7][C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:20])[CH:3]=1.C1(C)C=CC([S:27](=S)(O)=O)=CC=1.[CH3:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(OCC)C.C(O)C>[C:34]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][S:27][C:3]1[C:4](=[O:20])[O:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][C:2]=1[OH: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-6,6-diphenyl-2H-pyran-2-one (0.250 g, 0.94 mmol), (2-methylbiphenyl) -p-toluenethiosulfonate (0.389 g, 1.1 mmol), Et3N (0.26 ML, 1.9 mmol), absolute ethanol (5.0 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 thick oil (0.286 g). 1H NMR (400 MHz, DMSO-d6) δ 11.770 (bs, 1 H), 7.434-7.148 (m, 18 H), 6.969 (d, 1 H, J=7 Hz), 3.595 (s, 2 H), 3.407 (s, 2 H).

Workup

washwashed with H2O
customThe solvent was then removed in vacuo

Sources & evidence

ORD record: ord-fcc3fa515929476fa90bbeb24d514395
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840751

Reaction notes

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