Dimethyl Sulfoxide → 4,4-Dimethyl-5-methoxypent-1-ene

HRID 2120336Notes

Reaction equation

HRID 2120336 reaction equation
[H-].[Na+].CS(C)=O.[CH3:7][C:8]([CH3:14])([CH2:11][CH:12]=[CH2:13])[CH2:9][OH:10].[CH3:15]I>CCOCC.O>[CH3:15][O:10][CH2:9][C:8]([CH3:14])([CH3:7])[CH2:11][CH:12]=[CH2:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 107491582,2-Dimethylpent-4-en-1-ol

Product 1

HCID 234394984,4-Dimethyl-5-methoxypent-1-eneYield 25.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Under nitrogen, 2.211 g NaH was suspended in 50 mL dry ether in a three-necked round bottom flask. Anhydrous (CH3)2SO (5.0 mL) was added. The flask was cooled with ice. 2,2-Dimethyl-4-penten-1-ol(7.0 g) in 13 mL anhydrous ether was added dropwise through an addition funnel. The solution was then refluxed overnight. Upon cooling in ice, 43.56 g CH3I (5 eq) was added through an addition funnel. Soon a white precipitate was seen. The slurry was refluxed for 4 h. Upon cooling, water and ether were added to the mixture. The ether layer was separated, washed with water twice and dried with Na2SO4. Careful evaporation of ether (the product has a low b.p.) gave 2.0 g pure product. 1H NMR (CDCl3): δ 0.86 (s, 6H, —CMe2-); 2.00 (d, 2H, CH2═CH—CH2—); 3.05 (s, 2H, —CH2OMe); 3.33 (s, 3H, —CH2OMe); 5.00 (m, 2H, CH2═CH—); 5.80 (m, 1H, CH2═CH—).

Workup

  1. temperatureThe flask was cooled with ice
  2. temperatureThe solution was then refluxed overnight
  3. temperatureUpon cooling in ice
  4. temperatureThe slurry was refluxed for 4 h
  5. temperatureUpon cooling
  6. customThe ether layer was separated
  7. washwashed with water twice
  8. dry with materialdried with Na2SO4
  9. customCareful evaporation of ether (the product

Sources & evidence

ORD record
ord-d908dc94bc694072a86515502259d323
Source dataset
uspto-grants-2004_02
Patent number
US06689910B2

Reaction notes

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