Chlorotrimethylsilane → HCID 54737113, compound

HRID 2394034Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].Cl[Si](C)(C)C.[C:37]1([CH2:43][CH2:44][S:45][CH:46]([C:50](O)=[O:51])[C:47](O)=[O:48])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[K+].[Br-]>>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[O:20][C:47](=[O:48])[C:46]([S:45][CH2:44][CH2:43][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[C:50]([OH:51])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:8][CH:9]=1

Participants

Reactant 5

HCID 6397Chlorotrimethylsilane

HCID 253877Potassium Bromide

HCID 925838HCID 925838, compound

HCID 2733832Lithium Hexamethyldisilazide

HCID 19596072[(Phenylethyl)thio]propanedioic acid

Product 1

HCID 54737113HCID 54737113, compound

Procedure

The title compound was prepared by Method A using 4-[[(4-acetyl)phenoxy]methyl]benzoic acid methyl ester (2.0 g, 7.04 mmol), lithium hexamethyldisilazide (2.36 g, 14.08 mmol), chlorotrimethylsilane (2.38 g, 14.08 mmol) and diethyl ester of [(2-phenylethyl)thio]propanedioic acid (1.0 g, 3.05 mmol). m.p. 157°-158° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.78 (t, 2 H), 2.97 (t, 2 H), 3.86 (s, 2 H), 5.31 (s, 2 H), 6.67 (s, 1 H), 7.17 (q, 4 H), 7.25 (m, 3 H), 7.61 (d, 2 H), 7.78 (d, 2 H), 8.0 (d, 2 H); IR (KBr) 3023, 2936, 2581, 1632, 1510, 1404, 1258, 1184, 1098, 1009, 818, 718 cm-1 ; MS (CI) m/e 517 (M+29, 7), 489 (M+H, 55), 384 (19), 149 (40), 105 (100).

Sources & evidence

ORD record: ord-b5d56f1df72a49cb940eb655cf7655df
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808062

Reaction notes

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