Cyclohexanone, 3,3-dimethyl- → HCID 86681317, compound

HRID 1778887Notes

Reaction equation

HRID 1778887 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[Si](C)(C)C.C([Li])CCC.[CH3:16][C:17]1([CH3:24])[CH2:22][CH2:21][CH2:20][C:19](=O)[CH2:18]1>O1CCCC1.C(OCC)C>[CH3:16][C:17]1([CH3:24])[CH2:22][CH2:21][CH2:20][C:19](=[C:2]2[S:3][CH2:4][CH2:5][CH2:6][S:1]2)[CH2:18]1

Participants

6

Reactant 3

HCID 76322Cyclohexanone, 3,3-dimethyl-HCID 834132-Trimethylsilyl-1,3-dithianeHCID 178418339Butyllithium

Product 1

HCID 86681317HCID 86681317, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (1,3-dithian-2-yl)trimethylsilane (5.0 g) in tetrahydrofuran at −78° C. was added n-butyllithium (1.6M, 16.24 mL). After stirring for 30 minutes, 3,3-dimethylcyclohexanone (3.3 g) was added as a solution in tetrahydrofuran and the reaction mixture was allowed to warm to room temperature. The reaction mixture was diluted with diethyl ether (100 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with a gradient of 0.13% to 2.5% ether/hexanes gave the title compound.

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washSilica gel chromatography eluting with a gradient of 0.13% to 2.5% ether/hexanes

Sources & evidence

ORD record
ord-d4a7c9a5a7e14036b135fd7f7a4d19a9
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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