Triethylamine → 4-(4-Nitrophenyl)butyl methanesulfonate

HRID 1375720

Reaction equation

HRID 1375720 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5908694-Nitrobenzenebutanol

Product 1

HCID 147295324-(4-Nitrophenyl)butyl methanesulfonateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Nitrophenyl)-1-Butanol (2.5 g, 12.166 mmol) was dissolved in DCM (50 ml). The solution was cooled in an ice-bath. Triethylamine (2.45 ml, 15.2 mmol) was added and then methanesulfonyl chloride (1.533 g, 13.382 mmol) was dropped in. After 1 hour, the ice-bath was removed. The mixture was stirred for 4 hours more. The reaction mixture was washed with water, sodium hydrogencarbonate aqueous solution (1%) and water (×3) and dried with magnesium sulfate. The solvent was evaporated in vacuum and the desired product (3.25 g) was obtained, yield 98%.

Workup

  1. temperatureThe solution was cooled in an ice-bath
  2. customthe ice-bath was removed
  3. washThe reaction mixture was washed with water, sodium hydrogencarbonate aqueous solution (1%) and water (×3)
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-2fb8b0369a2348e2996f5f4b9ff85684
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Linked notes

Loading…