Chlorotrimethylsilane → 3-Benzylsulfanyl-4-hydroxy-6-[3-(trifluoromethoxy)phenyl]pyran-2-one

HRID 613105Notes

Reaction equation

HRID 613105 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[Li].C[Si]([NH-])(C)C.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.[K+].[Br-]>O>[OH:39][C:38]1[CH:11]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:13])([F:14])[F:1])[CH:5]=2)[O:12][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

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 253877Potassium BromideHCID 7371611-(3-(Trifluoromethoxy)phenyl)ethanoneHCID 3028194LithiumHCID 19596125[(Phenylmethyl)thio]propanedioic acidHCID 53627528(Trimethylsilyl)amide

Product 1

HCID 546813813-Benzylsulfanyl-4-hydroxy-6-[3-(trifluoromethoxy)phenyl]pyran-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared by Method A using 3'trifluoromethoxyacetophenone (3 g, 14.7 mmol), lithium bis(trimethylsilylamide (2.45 g, 14.7 mmol), chlorotrimethylsilane (2.47 g, 14.7 mmol) and diethyl ester of [(phenylmethyl)thio]propanedioic acid (1.00 g, 3.54 mmol). m.p. 128-132° C.; 1H NMR (400 MHz, DMSO-d6) δ4.03 (s, 2 H), 6.81 (s, 1 H), 7.2 (m, 2 H), 7.28 (m, 3 H), 7.56 (dd, 1 H), 7.69 (t, 1 H), 7.75 (s, 1 H), 7.86 (d, 1 H); IR (KBr) 2963, 1651, 1550, 1394, 1369, 1395, 1263, 1098, 1024, 800 cm-1 ; MS (CI): m/e 395 (M+H, 37), 309 (8), 273 (7), 205 (3), 119 (10); Analysis calc'd for C19H13O4S1F3.H2O: C, 55.34; H, 3.67; found: C, 54.94; H, 4.03.

Sources & evidence

ORD record
ord-71641938f47945f8b33c579e7dc4a091
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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