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

HRID 613058Notes

Reaction equation

HRID 613058 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].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:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[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 113402-MethylacetophenoneHCID 2733832Lithium HexamethyldisilazideHCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 546812793-Benzylsulfanyl-4-hydroxy-6-o-tolyl-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 2'-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). 1H NMR (400 MHz, DMSO-d6) δ2.34 (s, 3 H), 4.01 (s, 2 H), 6.32 (s, 1 H), 7.32 (m, 9H).

Sources & evidence

ORD record
ord-3af734b3bd8f42789dff0c69202c0c4c
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

Loading…