Triethylamine → 3-[[2-(Cyclopropylmethyl)phenyl]thio]-6-(3,5-dimethyl-phenyl)-4-hydroxy-2H-pyran-2-one

HRID 2394060Notes

Reaction equation

HRID 2394060 reaction equation
O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(N([CH2:18][CH3:19])CC)C.[CH:20]1([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][CH:31]([C:35]([OH:37])=O)[C:32]([OH:34])=[O:33])[CH2:22][CH2:21]1>C(Cl)Cl>[CH:20]1([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][C:31]2[C:32](=[O:33])[O:34][C:25]([C:24]3[CH:23]=[C:20]([CH3:22])[CH:21]=[C:18]([CH3:19])[CH:29]=3)=[CH:26][C:35]=2[OH:37])[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 19596062[[2-(Cyclopropylmethyl)phenyl]thio]propandioic acid

Product 1

HCID 546812193-[[2-(Cyclopropylmethyl)phenyl]thio]-6-(3,5-dimethyl-phenyl)-4-hydroxy-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 3,3'-dimethyl acetophenone (2 g, 13.51 mmol), trimethylsilyl triflate (3 g, 13.1 mmol), triethylamine (2.73 g, 27.02 mmol), methylene chloride (20 mL), and diethyl ester of [[2-(cyclopropylmethyl)phenyl]thio]propanedioic acid (2.18 g, 6.76 mmol). m.p. 168° C.; 1H NMR (400 MHz, DMSO-d6) δ 0.28 (d, 2H), 0.39 (dd, 2H), 1.13 (m, 1H), 2.36 (s, 6H), 2.67 (d, 2H), 6.85 (s, 1H), 6.92 (m, 1H), 7.11 (m, 2H), 7.22 (s, 1H), 7.33 (m, 1H), 7.47 (s, 2H).

Sources & evidence

ORD record
ord-d30742bd652e4da48e0b348f514a8265
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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