Chlorotrimethylsilane → HCID 54681274, compound

HRID 2394011Notes

Reaction equation

HRID 2394011 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:27]1([CH2:33][S:34][CH:35]([C:39](O)=[O:40])[C:36](O)=[O:37])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:11][C:36](=[O:37])[C:35]([S:34][CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:39]([OH:40])[CH:10]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 149211-(3,5-Dimethylphenyl)ethan-1-oneHCID 2733832Lithium HexamethyldisilazideHCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 54681274HCID 54681274, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 3',5'-dimethylacetophenone (0.785 g, 5.31 mmol), lithium bis(trimethylsilyl)amide (0.977 g, 5.84 mmol), chlorotrimethylsilane (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. 170° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.33 (s, 6 H), 3.99 (s, 2 H), 6.67 (s, 1 H), 7.21 (m, 6 H), 7.39 (s, 2 H).

Workup

  1. custom170° C.

Sources & evidence

ORD record
ord-b7f58f80c18a49f9ae5a8d09dcc33a02
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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