Water → HCID 75274366, compound

HRID 384987Notes

Reaction equation

HRID 384987 reaction equation
[CH3:1][CH:2]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH:3](O)[CH2:4][N+:5]([O-:7])=[O:6].S(Cl)(C)(=O)=O.C(N(CC)CC)C.O>ClCCl>[CH3:1][CH:2]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH:3]=[CH:4][N+:5]([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 49764771HCID 49764771, compound

Product 1

HCID 75274366HCID 75274366, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 9.0 g of 3,5-dimethyl-1-nitro-2-hexanol in 100 ml of dichloromethane, 6.5 g of mesyl chloride and 10.4 g of triethylamine were gradually dropped thereto at 4° C., respectively. The temperature of the solution was allowed to rise to room temperature, and the solution was stirred for 1.5 hours. Water was added to stop the reaction, and the solution was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and concentrated, and then purified by silica gel chromatography (hexane/ethyl acetate=10/1), thereby obtaining 6.8 g of 3,5-dimethyl-1-nitrohex-1-ene (yield: 83.9%).

Workup

  1. additionwere gradually dropped
  2. customat 4° C.
  3. customto rise to room temperature
  4. customthe reaction
  5. extractionthe solution was extracted with dichloromethane
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-3f2318cef9d44bc4ac23ad293295ce8b
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

Loading…