Chlorotrimethylsilane → 4-hydroxy-6-(4-hydroxyphenyl)-3-[(2-phenylethyl)sulfanyl]-2H-pyran-2-one

HRID 613061Notes

Reaction equation

HRID 613061 reaction equation
[OH: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][CH2:33][S:34][CH:35]([C:39](O)=[O:40])[C:36](O)=[O:37])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[OH:40][C:39]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[O:10][C:36](=[O:37])[C:35]=1[S:34][CH2:33][CH2:32][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 74694'-HydroxyacetophenoneHCID 2733832Lithium HexamethyldisilazideHCID 19596072[(Phenylethyl)thio]propanedioic acid

Product 1

HCID 546812234-hydroxy-6-(4-hydroxyphenyl)-3-[(2-phenylethyl)sulfanyl]-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 4'-hydroxyacetophenone (0.688 g, 5.06 mmol), lithium bis(trimethylsilyl)amide (1.84 g, 11.1 mmol), chlorotrimethylsilane (1.41 mL, 11.1 mmol), THF (111 mL), and diethyl ester of [(2-phenylethyl)thio]propanedioic acid (1.00 g, 3.37 mmol). 1H NMR (400 MHz, DMSO-d6) δ2.78 (t, 2 H), 2.95 (t, 2 H), 6.62 (s, 1 H), 6.89 (dd, 2 H), 7.21 (m, 5 H), 7.65 (d, 2 H), 10.22 (s, 1 H), 11.05 (bs, 1 H).

Sources & evidence

ORD record
ord-8719bd80836f4b37a9d79224f0f58aaf
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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