Methanesulfonyl chloride → HCID 20230972, compound

HRID 2290498Notes

Reaction equation

HRID 2290498 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:11][CH:10]([CH3:12])[C:9]([CH3:14])([CH3:13])[C:8]2[CH2:7][C:6]([CH3:16])(O)[CH:5](O)[CH2:4][C:3]1=2.CS(Cl)(=O)=O>N1C=CC=CC=1.CCOCC>[CH3:1][C:2]1([CH3:18])[CH2:11][CH:10]([CH3:12])[C:9]([CH3:14])([CH3:13])[C:8]2[CH2:7][CH:6]([CH3:16])[CH2:5][CH2:4][C:3]1=2

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20230960HCID 20230960, compound

Product 1

HCID 20230972HCID 20230972, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

85 g (0.337 mol) of the 2,2,4,5,5,8-hexamethyl-bicyclo[4.4.0]dec-1(6)-ene-8,9-diol are dissolved at room temperature in 218 ml of pyridine. The solution is now cooled to 0° C. and 30.2 ml of methanesulphonyl chloride are slowly added dropwise during 20 minutes. The mixture is stirred at room temperature for a further 24 hours. The mixture is thereupon diluted with ether and washed with 1.480 l of 2N hydrochloric acid and 400 ml of saturated sodium chloride solution. The aqueous phase is extracted with ether and the combined organic phases are washed neutral with dilute sodium bicarbonate solution, dried over sodium sulphate and evaporated.

Workup

  1. washwashed with 1.480 l of 2N hydrochloric acid and 400 ml of saturated sodium chloride solution
  2. extractionThe aqueous phase is extracted with ether
  3. washthe combined organic phases are washed neutral with dilute sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-3b85e8c2a0f74f34984a16e6c13295f4
Source dataset
uspto-grants-1986_10
Patent number
US04617146

Reaction notes

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