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

HRID 2393983Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:16]1([CH2:22][S:23][CH:24]([C:28]([OH:30])=O)[C:25]([OH:27])=[O:26])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:31]1[CH2:35]O[CH2:33][CH2:32]1>>[OH:30][C:28]1[CH:33]=[C:32]([CH2:31][CH2:35][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:27][C:25](=[O:26])[C:24]=1[S:23][CH2:22][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Reactant 4

HCID 6397Chlorotrimethylsilane

HCID 8028Tetrahydrofuran

HCID 2733832Lithium Hexamethyldisilazide

HCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 547114834-Hydroxy-6-(2-phenylethyl)-3-[(phenylmethyl)thio]-2H-pyran-2-one

Procedure

The title compound was prepared by Method A using 4-phenethylacetophenone (0.786 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. 164°-166° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.75 (t, 3 H), 2.85 (t, 2 H), 3.92 (s, 2 H), 5.92 (s, 1 H), 7.23 (m, 9H), 11.69 (bs, 1 H).

Sources & evidence

ORD record: ord-c6073e10dd5d4bd5b32b2e4bd05b7c4f
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808062

Reaction notes

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