Chlorotrimethylsilane → HCID 15101118, compound

HRID 704585Notes

Reaction equation

HRID 704585 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C([N-]C(C)C)(C)C.[Li+].[CH3:21][Si:22](Cl)([CH3:24])[CH3:23]>O1CCCC1>[CH3:21][Si:22]([CH3:24])([CH3:23])[O:1][C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 15101118HCID 15101118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 4-oxocyclohexanecarboxylate (5.95 g) (Example B) in 200 ml of anhydrous tetrahydrofuran is added dropwise under nitrogen to a solution of lithium diisopropylamide (prepared from 4.40 g of diisopropylamine and 26.2 ml of 1.6 M n-butyllithium hexane solution) in 200 ml of tetrahydrofuran at -78° C. The mixture is stirred at this temperature for one hour and trimethylsilyl chloride (4.71 g) is added dropwise via syringe. The reaction mixture is allowed to warm to room temperature overnight and the solvent evaporated in vacuo. The residue is triturated with 100 ml of diethyl ether and filtered to remove inorganic salts. Evaporation of the volatile components of the mixture gives ethyl 4-[(trimethylsilyl)oxy]-3-cyclohexene-1-carboxylate as a colorless oil which is reacted with N-bromosuccinimide and thiourea by following the procedure of Example 1 (Method A) to yield the title compound as a white solid; mp 170°-173° C.

Workup

  1. customthe solvent evaporated in vacuo
  2. customThe residue is triturated with 100 ml of diethyl ether
  3. filtrationfiltered
  4. customto remove inorganic salts
  5. customEvaporation of the volatile components of the mixture

Sources & evidence

ORD record
ord-124b36796918445dbbc00a43e8f5da95
Source dataset
uspto-grants-1991_01
Patent number
US04988699

Reaction notes

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