Chlorotrimethylsilane → HCID 54681428, compound

HRID 2394010Notes

Reaction equation

HRID 2394010 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[CH3:20].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:36]1([CH2:42][CH2:43][S:44][CH:45]([C:49](O)=[O:50])[C:46](O)=[O:47])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1COCC1>[OH:50][C:49]1[CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[C:12]([CH3:20])[CH:13]=2)[O:19][C:46](=[O:47])[C:45]=1[S:44][CH2:43][CH2:42][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 2733832Lithium HexamethyldisilazideHCID 19596072[(Phenylethyl)thio]propanedioic acidHCID 19596145HCID 19596145, compound

Product 1

HCID 54681428HCID 54681428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 4'-[(2-methoxyphenyl)methoxy]-3'-methylacetophenone (1.36 g, 5.06 mmol), lithium bis(trimethylsilyl)amide (0.930 g, 5.56 mmol), chlorotrimethylsilane (0.705 mL, 5.56 mmol), THF (56 mL), and diethyl ester of [(2-phenylethyl)thio]propanedioic acid (1.00 g, 3.37 mmol). m.p. dec. 170° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.25 (s, 3 H), 2.77 (t, 2 H), 2.97 (t, 2 H), 3.84 (s, 3 H), 5.17 (s, 2 H), 6.67 (s, 1 H), 6.98 (t, 1 H), 7.70 (d, 1 H), 7.27 (m, 6 H), 7.41 (t, 1 H), 7.43 (d, 1 H), 7.65 (m, 2 H), 11.81 (bs, 1 H).

Workup

  1. custom170° C.

Sources & evidence

ORD record
ord-3b457b03a1d54ba7b4d8d4adf0793ec0
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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