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

HRID 2393975Notes

Reaction equation

HRID 2393975 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:29]1([CH2:35][S:36][CH:37]([C:41](O)=[O:42])[C:38](O)=[O:39])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[OH:42][C:41]1[CH:2]=[C:1]([C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=2)[O:3][C:38](=[O:39])[C:37]=1[S:36][CH2:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 71222-AcetylnaphthaleneHCID 2733832Lithium HexamethyldisilazideHCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 546813104-Hydroxy-6-(2-naphthalenyl)-3-[(phenylmethyl)thio]-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 2-acetyl naphthalene (1.97 g, 11.6 mmol), lithium bis(trimethylsilyl)amide (2.13 g, 12.76 mmol), chlorotrimethylsilane (1.61 mL, 12.76 mmol), THF (127 mL), and diethyl ester of [(phenylmethyl)thio]-propanedioic acid (2.90 g, 10.5 mmol). m.p. dec. 203° C.; 1H NMR (250 MHz, DMSO-d6) δ 4.04 (s, 2 H), 6.89 (s, 1 H), 7.23 (in, 5 H), 7.61 (m, 2 H), 7.84 (d, 2 H), 8.05 (m, 3 H), 8.43 (s, 1 H), 11.95 (bs, 1 H).

Workup

  1. custom203° C.

Sources & evidence

ORD record
ord-1191f89d587a42c89495968f388dab72
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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