Triethylamine → 6-(3,5-Dichlorophenyl)-4-hydroxy-3-[(2-isopropylphenyl)thio]-2H-pyran-2-one

HRID 613144Notes

Reaction equation

HRID 613144 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[CH:5]=1)=[O:3].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:11][C:6]1[CH:5]=[C:4]([C:2]2[O:3][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:1]=2)[CH:9]=[C:8]([Cl:10])[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 27580583',5'-DichloroacetophenoneHCID 19596178[(2-Isopropylphenyl)thio)propanedioic acid

Product 1

HCID 546813156-(3,5-Dichlorophenyl)-4-hydroxy-3-[(2-isopropylphenyl)thio]-2H-pyran-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 3,5-dichloroacetophenone (2 g, 10.58 mmol), trimethylsilyl triflate (2.35 g, 10.58 mmol), triethylamine (2.14 g, 21.16 mmol), methylene chloride (20 mL), and diethyl ester of [(2-isopropylphenyl)thio]propanedioic acid (1.64 g, 5.29 mmol). Isolated yield: 70% m.p.168-169° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.25 (d, 6H), 3.42 (m, 1H), 6.92 (d, 1H), 7.01 (s, 1H), 7.06 (t, 1H), 7.13 (t, 1H), 7.28 (d, 1H), 7.83 (m, 1H), 7.88 (m, 2H).

Workup

  1. customIsolated yield: 70% m.p.168-169° C.

Sources & evidence

ORD record
ord-7b7e90f104a74759b520095c76acdeba
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

Loading…