Chlorotrimethylsilane → 3-Benzylsulfanyl-4-hydroxy-6-p-tolyl-pyran-2-one

HRID 2393979Notes

Reaction equation

HRID 2393979 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:26]1([CH2:32][S:33][CH:34]([C:38](O)=[O:39])[C:35](O)=[O:36])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[OH:39][C:38]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[O:10][C:35](=[O:36])[C:34]=1[S:33][CH2:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8500p-METHYLACETOPHENONEHCID 2733832Lithium HexamethyldisilazideHCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 546811933-Benzylsulfanyl-4-hydroxy-6-p-tolyl-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 4'-methylacetophenone (0.712 g, 5.31 mmol), lithium bis(trimethylsilyl)amide (0.977 g, 5.84 mmol), chlorotrimethylsilane (0.741 mL, 5.84 mmol), THF (58 mL), and diethyl ester of [(phenylmethyl)thio]-propanedioic acid (1.00 g, 3.54 mmol). m.p. dec. 205° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.37 (s, 3 H), 3.99 (s, 2 H), 6.69 (s, 1 H), 7.26 (m, 7 H), 7.68 (m, 2 H), 11.83 (bs, 1 H).

Workup

  1. custom205° C.

Sources & evidence

ORD record
ord-7c15663b90fa4c659c91a8a35a286013
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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