Cesium fluoride → HCID 90203783, compound

HRID 1480178Notes

Reaction equation

HRID 1480178 reaction equation
[CH2:1]([O:8][CH2:9]/[C:10](=[N:12]/[S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])/[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+].C[Si]([C:25]#[N:26])(C)C>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C:10]([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])([C:25]#[N:26])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 82115Trimethylsilyl cyanideHCID 90203394HCID 90203394, compound

Product 1

HCID 90203783HCID 90203783, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-N-(1-(benzyloxy)propan-2-ylidene)-2-methylpropane-2-sulfinamide (CAN 393536-49-7, 3.1 g, 11.6 mmol) in dry THF (55 ml) under an argon atmosphere was added cesium fluoride (1.94 g, 12.8 mmol) followed by addition of trimethylsilyl cyanide (1.27 g, 1.71 ml, 12.8 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and poured into a separatory funnel. Organic phase was extracted with a 1M aqueous solution of sodium bicarbonate and the organic phase was collected. The aqueous phase was back-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (2.53 gr, 74%); MS (ESI, m/z): 295.6 (M+H+).

Workup

  1. additionpoured into a separatory funnel
  2. extractionOrganic phase was extracted with a 1M aqueous solution of sodium bicarbonate
  3. customthe organic phase was collected
  4. extractionThe aqueous phase was back-extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated down to dryness
  7. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-ae02c22bbd5840fda9226a142e7bbab6
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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