Chlorotrimethylsilane → HCID 54681481, compound

HRID 2394020Notes

Reaction equation

HRID 2394020 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:25]1([CH2:31][CH2:32][S:33][CH:34]([C:38](O)=[O:39])[C:35](O)=[O:36])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[OH:39][C:38]1[CH:2]=[C:1]([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)[O:3][C:35](=[O:36])[C:34]=1[S:33][CH2:32][CH2:31][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 142824-AcetylpyridineHCID 2733832Lithium HexamethyldisilazideHCID 19596072[(Phenylethyl)thio]propanedioic acid

Product 1

HCID 54681481HCID 54681481, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 4-acetylpyridine (2.50 g, 20.63 mmol), lithium bis(trimethylsilyl)amide (5.17 g, 30.94 mmol), chlorotrimethylsilane (3.92 mL, 30.94 mmol), THF (200 mL), and diethyl ester of [(2-phenylethyl)thio]-propanedioic acid (1.00 g, 3.37 mmol). m.p. dec. 149°-152° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.78 (t, 2 H), 3.04 (t, 2 H), 6.98 (s, 1 H), 7.20 (m, 5 H), 7.74 (d, 2 H), 8.74 (d, 2 H).

Workup

  1. custom149°-152° C.

Sources & evidence

ORD record
ord-0bb816ff70114bcbbb5453e71f62257c
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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