Chlorotrimethylsilane → HCID 54711484, compound

HRID 2394029Notes

Reaction equation

HRID 2394029 reaction equation
[CH3:1][C:2]([C:4]1[CH:13]=[CH:12][C:7]2[O:8][CH:9]=[CH:10][O:11][C:6]=2[CH:5]=1)=[O:3].[Li].C[Si]([NH-])(C)C.Cl[Si](C)(C)C.[C:25]1([CH2:31][S:32][CH:33]([C:37](O)=[O:38])[C:34](O)=[O:35])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[K+].[Br-]>>[O:8]1[C:7]2[CH:12]=[CH:13][C:4]([C:2]3[O:3][C:34](=[O:35])[C:33]([S:32][CH2:31][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:37]([OH:38])[CH:1]=3)=[CH:5][C:6]=2[O:11][CH2:10][CH2:9]1

Participants

7

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 253877Potassium BromideHCID 3028194LithiumHCID 19596124HCID 19596124, compoundHCID 19596125[(Phenylmethyl)thio]propanedioic acidHCID 53627528(Trimethylsilyl)amide

Product 1

HCID 54711484HCID 54711484, compound

Procedure

The title compound was prepared by Method A using 1,4-benzodioxin-6-yl methyl ketone (2.5 g, 14.25 mmol), lithium bis(trimethylsilylamide (2.35 g, 14.25 mmol), chlorotrimethylsilane (2.47 g, 14.25 mmol) and diethyl ester of [(phenylmethyl)thio]propanedioic acid (1.00 g, 3.55 mmol). m.p. 192°-193° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.99 (s, 2 H), 4.17 (m, 4 H), 6.8 (s, 1 H), 7.0 (d, 1 H), 7.2 (m, 1 H), 2.28 (m, 7 H); IR (KBr) 3435, 2924, 1649, 1624, 1508, 1288, 1066, 698 cm-1 ; MS (CI): m/e 369 (M+H,), 277 (12), 233 (12), 163 (9), 107 (10), 91 (76); Analysis calc'd for C20H16O5S1 : C, 65.21; H, 4.38; found: C, 64.80; H, 4.17.

Sources & evidence

ORD record
ord-df82f2edf31343a0a02d95a17ae04768
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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