Triethylamine → 6-(3,5-Dimethylphenyl)-4-hydroxy-3-(2-isopropylphenyl)sulfanyl-pyran-2-one

HRID 613124Notes

Reaction equation

HRID 613124 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(N(CC)CC)C.[CH:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[S:40][CH:41]([C:45](O)=[O:46])[C:42](O)=[O:43])([CH3:33])[CH3:32]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:11][C:42](=[O:43])[C:41]([S:40][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[CH:31]([CH3:32])[CH3:33])=[C:45]([OH:46])[CH:10]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 149211-(3,5-Dimethylphenyl)ethan-1-oneHCID 65367Trimethylsilyl triflateHCID 19596178[(2-Isopropylphenyl)thio)propanedioic acid

Product 1

HCID 546814866-(3,5-Dimethylphenyl)-4-hydroxy-3-(2-isopropylphenyl)sulfanyl-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 3', 5'-dimethylacetophenone (0.714 g, 4.83 mmol), trimethylsilyl triflate (1.12 mL, 5.79 mmol), triethylamine (1.34 mL, 9.66 mmol), methylene chloride (17 mL), and diethyl ester of [(2-isopropylphenyl)thio]propanedioic acid (1.00 g, 3.22 mmol) m.p. 154-155° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.24 (d, 6H), 2.35 (s, 6H), 3.40 (m, 1H), 6.90 (d, 1H), 7.05 (t, 1H), 7.11 (dt, 2H), 7.20 (s, 1H), 7.27 (d, 1H), 7.45 (s, 2H).

Sources & evidence

ORD record
ord-5db7e3baf62e41948d82410dcb1f37da
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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