Triethylamine → 6-(3,4-Dichloro-phenyl)-4-hydroxy-3-(2-isopropyl-phenylsulfanyl)-pyran-2-one

HRID 2394054Notes

Reaction equation

HRID 2394054 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].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>[Cl: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]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 19596178[(2-Isopropylphenyl)thio)propanedioic acid

Product 1

HCID 546812606-(3,4-Dichloro-phenyl)-4-hydroxy-3-(2-isopropyl-phenylsulfanyl)-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 3',4'-dichloroacetophenone (2.46 g, 12.8 mmol), trimethylsilyl triflate (3.0 mL, 15.4 mmol), triethylamine (3.6 mL, 26.0 mmol), methylene chloride (30 mL), and diethyl ester of [(2-isopropylphenyl)thio] propanedioic acid (4.0 g, 12.8 mmol) m.p. 204°-207° C.; 1H NMR (400 MHz, CDCl3) δ 1.33 (d, 6H), 3.55 (m, 1H), 6.71 (s, 1H), 7.00 (m, 1H), 7.08 (m, 1H), 7.20 (m, 1H), 7.30 (m, 1H), 7.56 (d, 1H), 7.69 (m, 1H), 7.74 (br, 1H), 7.98 (s, 1H).

Sources & evidence

ORD record
ord-a3cb6f83b0f7453393d4500de18ee5d4
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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