Sodium hydride → HCID 22026340, compound

HRID 1793227Notes

Reaction equation

HRID 1793227 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[H][H].[CH3:11][C:12]1[C:13](=[O:24])[C:14]([CH3:23])([CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH2:15][CH2:16][CH:17]=1>CS(C)=O.O>[CH3:11][C:12]12[CH2:4][CH:17]1[CH2:16][CH2:15][C:14]([CH3:23])([CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[C:13]2=[O:24]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 115792582,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclo-hex-2-enoneHCID 178418361HCID 178418361, compound

Product 1

HCID 22026340HCID 22026340, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sodium hydride (60%, 2.11 g, 52.8 mmol) was added to a suspension of trimethylsulfoxonium iodide (11.6 g, 52.8 mmol) in 60 ml of dimethyl sulfoxide. The mixture was stirred for 30 min until hydrogen evolution stopped. 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone was added and the mixture was stirred over night at room temperature, was then diluted with water and extracted with pentane. The organic phase was washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled (bp.95° C./0.05 Torr) to yield 4.5 g (83%) of product as a mixture of two diastereomers. 1H-NMR (200 MHz, CDCl3): 5.11-4.93 (m, 1H, 2′-H), 2.45-1.32 (m, 7H), 1.75/1.70 (2s, 3H, 4′H), 1.63/1.59 (2s, 3H, 3′-CH3), 1.31-1.16 (m, 1H), 1.23/1.21 (2s, 3H), 1.01/0.99 (2s, 3H), 0.75-0.64 (m, 1H) ppm. GC/MS (EI): 206 (M+, 12), 191 (14), 163 (20), 138 (90), 123 (100), 109 (34), 95 (57), 69 (62), 41 (94). IR (ATR): 2962s, 2928s, 2866s, 1681vs, 1451s, 1375m, 1043m, 1000m cm−1.

Workup

  1. extractionextracted with pentane
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. distillationThe residue was distilled (bp.95° C./0.05 Torr)

Sources & evidence

ORD record
ord-00827ff276b54f969f5cbc888a5ba452
Source dataset
uspto-grants-2006_07
Patent number
US07078570B2

Reaction notes

Loading…