Methanesulfonate → HCID 23039727, compound

HRID 2166412Notes

Reaction equation

HRID 2166412 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([O:15][CH2:16][CH3:17])([CH2:12][CH2:13][CH3:14])[CH2:10][OH:11].[S:18]([O-])(=[O:21])(=[O:20])[CH3:19]>N1C=CC=CC=1>[CH3:19][S:18]([O:11][CH2:10][C:9]([O:15][CH2:16][CH3:17])([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH2:12][CH2:13][CH3:14])(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 85257MethanesulfonateHCID 23039690HCID 23039690, compound

Product 1

HCID 23039727HCID 23039727, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.93 g (25 mmoles) of 2-(2,4-dichlorophenyl)-2-ethoxy-pentan-1-ol are dissolved in 20 ml of pyridine and converted into the corresponding mesylate by adding 3.15 g (27.5 mmoles) of methanesulfochloride. The reaction takes place exothermically with the precipitation of pyridine hydrochloride. After a reaction time of 1 hour, water is added and the mixture is extracted with diethyl ether. The combined extracts are washed with half-saturated sodium chloride solution, dried over sodium sulfate, filtered and freed from solvent in vacuo. Yield 8.6 g. 100 MHz-1H-NMR (CDCl3): δ=4.7 ppm ##STR37## 3.2-3.6 ppm (q, 2H, --OCH2CH3); 2.8 ppm (s, 3H, --OSO2CH3); 1.8-2.5 ppm (m, 2H, --CH2CH2CH3); 1.3 ppm (t, 3H, --OCH2CH3); 0.7-1.3 ppm (m, 5H, --CH2CH2CH3).

Workup

  1. additionby adding 3.15 g (27.5 mmoles) of methanesulfochloride
  2. customexothermically with the precipitation of pyridine hydrochloride
  3. additionAfter a reaction time of 1 hour, water is added
  4. extractionthe mixture is extracted with diethyl ether
  5. washThe combined extracts are washed with half-saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f3ccfdc3dc1a479195ad3d7b3525ae9b
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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