Sodium Bicarbonate → 2-Methyl-propane-2-sulfinic acid 1-[4-(tert-butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexyl]-methylideneamide

HRID 1948163Notes

Reaction equation

HRID 1948163 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH:7]1[CH2:12][CH2:11][C:10]([C:15]([F:18])([F:17])[F:16])([CH:13]=O)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]([S:25]([NH2:27])=[O:26])([CH3:24])[CH3:23].C([O-])(O)=O.[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.C1COCC1>[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH:7]1[CH2:12][CH2:11][C:10]([CH:13]=[N:27][S:25]([C:22]([CH3:24])([CH3:23])[CH3:21])=[O:26])([C:15]([F:18])([F:17])[F:16])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 583808634-(tert-Butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexanecarbaldehyde

Product 1

HCID 670727972-Methyl-propane-2-sulfinic acid 1-[4-(tert-butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexyl]-methylideneamideYield 91.5%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.20 g (10.3 mmol) of 4-(tert-Butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexanecarbaldehyde (71) were dissolved using 25 ml of anhydrous THF. 1.31 g (10.8 mmol) of 2-methyl-2-propanesulfinamide and 4.32 ml (20.6 mmol) of titanium (IV) ethoxide were added and the mixture heated for 4 h at reflux. The reaction mixture was poured into 75 ml of a saturated aqueous solution of NaHCO3 and the precipitate removed by filtration. The filtrate was extracted three times using 50 ml of ethyl acetate each. The organic layer was dried using MgSO4 and evaporated to yield 3.90 g of 72. Rt=1.02 min (Method Q).

Workup

  1. temperaturethe mixture heated for 4 h
  2. temperatureat reflux
  3. customthe precipitate removed by filtration
  4. extractionThe filtrate was extracted three times
  5. customThe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-5872c57fd1974c2193e72758514b2403
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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