Chlorotrimethylsilane → HCID 54681313, compound

HRID 2394017Notes

Reaction equation

HRID 2394017 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:33]1([CH2:39][CH2:40][S:41][CH:42]([C:46](O)=[O:47])[C:43](O)=[O:44])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[CH:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[O:17][C:43](=[O:44])[C:42]([S:41][CH2:40][CH2:39][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[C:46]([OH:47])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 2733832Lithium HexamethyldisilazideHCID 13340058HCID 13340058, compoundHCID 19596072[(Phenylethyl)thio]propanedioic acid

Product 1

HCID 54681313HCID 54681313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 4'-(cyclohexylmethoxy)acetophenone (2.50 g, 10.77 mmol), lithium bis(trimethylsilyl)amide (2.70 g, 16.16 mmol), chlorotrimethylsilane (2.05 mL, 16.16 mmol), THF (107 mL), and diethyl ester of [(2-phenylethyl)thio]propanedioic acid (1.00 g, 3.37 mmol). m.p. 130°-132° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.15 (m, 5 H), 1.81 (m, 6 H), 2.77 (t, 2 H), 2.97 (t, 2 H), 3.85 (d, 2 H), 6.67 (s, 1 H), 7.21 (m, 5 H), 7.45 (q, 1 H), 7.74 (d, 2 H).

Sources & evidence

ORD record
ord-c5337ffd86fe479ba4f979fd016e7222
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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