Chlorotrimethylsilane → 4-Hydroxy-6-[4-(2-phenylethoxy)phenyl]-3-[(2-phenylethyl)thio]-2H-pyran-2-one

HRID 613063Notes

Reaction equation

HRID 613063 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:34]1([CH2:40][CH2:41][S:42][CH:43]([C:47](O)=[O:48])[C:44](O)=[O:45])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1>[OH:48][C:47]1[CH:17]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:15][CH:14]=2)[O:18][C:44](=[O:45])[C:43]=1[S:42][CH2:41][CH2:40][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 2733832Lithium HexamethyldisilazideHCID 133400571-[4-(2-Phenylethoxy)phenyl]ethanoneHCID 19596072[(Phenylethyl)thio]propanedioic acid

Product 1

HCID 546812884-Hydroxy-6-[4-(2-phenylethoxy)phenyl]-3-[(2-phenylethyl)thio]-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 4'-(2-phenylethoxy)acetophenone (1.21 g, 5.06 mmol), lithium bis(trimethylsilyl)amide (0.930 g, 5.56 mmol), chlorotrimethylsilane (0.705 mL, 5.56 mmol), THF (57 mL), and diethyl ester of [(2-phenylethyl)thio]propanedioic acid (1.00 g, 3.37 mmol). m.p. 103-106° C.; 1H NMR (400 MHz, DMSO-d6) δ2.76 (t, 2 H), 2.97 (t, 2 H), 3.06 (t, 2 H), 4.27 (t, 2 H), 6.67 (s, 1 H), 7.21 (m, 12 H), 7.73 (d, 2 H).

Sources & evidence

ORD record
ord-628d09a31bf7412dbaf6bd898525f7da
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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