Dimethyl Sulfoxide → HCID 14798966, compound

HRID 345867Notes

Reaction equation

HRID 345867 reaction equation
CS(C)=[O:3].[I-].C[S+](C)C.[H-].[Na+].C(C1([CH:17]([C:34]2[CH:39]=[CH:38][CH:37]=CC=2)[CH2:18][C:19]([CH2:21][CH:22]([C:28]2C=CC=CC=2)[C:23]2([C:26]#[N:27])[CH2:25][CH2:24]2)=O)CC1)#N>O>[C:26]([C:23]1([C:22]2([CH2:21][CH2:19][C:18]3[CH:17]=[CH:34][CH:39]=[CH:38][CH:37]=3)[CH2:28][O:3]2)[CH2:24][CH2:25]1)#[N:27]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 131717042HCID 131717042, compound

Product 1

HCID 14798966HCID 14798966, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

10 ml of abs. DMSO are added dropwise at 10° C. to 2 g (10 mmol) of trimethylsulphonium iodide and 0.2 g (7 mmol) of sodium hydride (80% in oil). The mixture is stirred for 1 h at 20° C. After this, a solution of 1 g (5 mmol) of 1-cyanocyclopropyl 2-phenylethyl-ketone (compound II-16, Example 32) in 5 ml of abs. DMSO is added dropwise and the mixture is allowed to react for 4 h at 20° C. The solution is poured into water and extracted using ethyl acetate, the organic phase is dried with Na2SO4 and the solvent is evaporated in vacuo. 0.8 g (75% of theory) is obtained in the form of a colorless oil,

Workup

  1. customto react for 4 h at 20° C
  2. extractionextracted
  3. dry with materialthe organic phase is dried with Na2SO4
  4. customthe solvent is evaporated in vacuo
  5. custom0.8 g (75% of theory) is obtained in the form of a colorless oil

Sources & evidence

ORD record
ord-7874f95485e04b5d80e5c91c66f27c5e
Source dataset
uspto-grants-1991_10
Patent number
US05059615

Reaction notes

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