Chlorotrimethylsilane → HCID 54681500, compound

HRID 613100Notes

Reaction equation

HRID 613100 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([N-]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>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:11][C:35](=[O:36])[C:34]([S:33][CH2:32][CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:38]([OH:39])[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 2724682Lithium diisopropylamideHCID 19596072[(Phenylethyl)thio]propanedioic acid

Product 1

HCID 54681500HCID 54681500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 3',5'-dimethyl acetophenone (1.75 g, 11.82 mmol), lithium diisopropylamide (1.89 g, 17.73 mmol), chlorotrimethylsilane (2.25 mL, 17.73 mmol), THF (120 mL), and diethyl ester of [(2-phenylethyl)thio]-propanedioic acid (1.00 g, 3.37 mmol). m.p. 155-157° C.; 1H NMR (400 MHz, DMSO-d6) δ2.34 (s, 6 H), 2.77 (t, 2 H), 2.99 (t, 2 H), 6.72 (s, 1 H), 7.21 (m, 6 H), 7.41 (s, 2 H), 8.74 (d, 2 H).

Sources & evidence

ORD record
ord-deec51da2eb9449e8b0030d22efda451
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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