Chlorotrimethylsilane → HCID 54718674, compound

HRID 2394007Notes

Reaction equation

HRID 2394007 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:34]1([CH2:40][S:41][CH:42]([C:46](O)=[O:47])[C:43](O)=[O:44])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1>[C:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[O:18][C:43](=[O:44])[C:42]([S:41][CH2:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:46]([OH:47])[CH:17]=2)=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 569606HCID 569606, compoundHCID 2733832Lithium HexamethyldisilazideHCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 54718674HCID 54718674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 4'-benzoyloxyacetophenone (1.27 g, 5.31 mmol), lithium bis(trimethyl-silyl)amide (0.977 g, 5.84 mmol), chlorotrimethyl-silane (0.741 mL, 5.84 mmol), THF (58 mL), and diethyl ester of [(phenylmethyl)thio]propanedioic acid (1.00 g, 3.54 mmol). m.p. dec. 205° C.; 1H NMR (400 MHz, DMSO-d6) δ 4.01 (s, 2 H), 6.75 (s, 1 H), 7.21 (m, 1 H), 7.25 (d, 4 H), 7.47 (d, 2 H), 7.63 (t, 2 H), 7.77 (t, 1 H), 7.90 (d, 2 H), 8.16 (d, 2 H).

Workup

  1. custom205° C.

Sources & evidence

ORD record
ord-b749a6f482f74d10abd35d46e6453e6a
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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