2-Trimethylsilyl-1,3-dithiane → 2-(4,4-Dimethylcyclohexylidene)-1,3-dithiane

HRID 2055178Notes

Reaction equation

C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.C([Li])CCC.[CH3:16][C:17]1([CH3:24])[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1>C1COCC1>[CH3:16][C:17]1([CH3:24])[CH2:22][CH2:21][C:20](=[C:3]2[S:8][CH2:7][CH2:6][CH2:5][S:4]2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-trimethylsily-1,3-dithiane (42.3 g, 0.22 mol) in THF (400 mL) at 0° C. under an argon atmosphere was added a solution of n-butyl lithium (2.5 M in hexanes, 88 mL, 0.22 mol) and the mixture was cooled to −78° C. A solution of 4,4-dimethyl cyclohexanone (13.9 g, 0.11 mol) in THF (50 mL) was added over 10 min. After 2 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (200 mL). The aqueous phase was extracted with EtOAc (200 mL×2) and the combined organic layers were dried (MgSO4) and were evaporated. The reaction by-products were removed by vacuum distillation to yield the desired product as a white wax (21 g, 85%). MH+229

Workup

customAfter 2 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (200 mL)
extractionThe aqueous phase was extracted with EtOAc (200 mL×2)
dry with materialthe combined organic layers were dried (MgSO4)
customwere evaporated
customThe reaction by-products were removed by vacuum distillation

Sources & evidence

ORD record: ord-5325efedf5b4485caf06b4eab9953628
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332485B2

Reaction notes

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