Water → HCID 75274365, compound

HRID 384986Notes

Reaction equation

HRID 384986 reaction equation
[CH3:1][CH:2]([CH2:9][CH2:10][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][CH2:10][CH3:11])[CH:3]=[CH:4][N+:5]([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 49764651HCID 49764651, compound

Product 1

HCID 75274365HCID 75274365, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 15.0 g of 3-methyl-1-nitro-2-hexanol in 100 ml of dichloromethane, 11.7 g of mesyl chloride and 18.8 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 an hour. 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 9.0 g of 3-methyl-1-nitrohex-1-ene (yield: 81.4%).

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-a28ee0867c584b91aeac0b5f14419992
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

Loading…