Diethyl Ether → HCID 18786134, compound

HRID 1107874Notes

Reaction equation

HRID 1107874 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:11]([CH2:12][CH2:13]O)=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].C(N(CC)CC)C.C(OCC)C.[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>O>[CH3:1][C:2]1[O:3][C:4]2[C:11]([CH2:12][CH2:13][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18786148HCID 18786148, compound

Product 1

HCID 18786134HCID 18786134, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-30 °C

Procedure

5.1 g (26.5 mmol) of 2,3-dimethyl-7-(2-hydroxyethyl)benzofuran, 5.91 ml (42.5 mmol) of triethylamine and 500 ml of anhydrous ethyl ether are introduced, under an inert atmosphere, into a 1 l round-bottomed flask. The mixture is cooled to -30° C. and 3.3 ml (42.5 mmol) of mesyl chloride are added dropwise. The reaction mixture is stirred for 1 h 30, while being allowed to return to 0° C. 200 ml of water are added and extraction is carried out with ethyl ether. The organic phases are combined and concentrated under vacuum. 7.48 g of 2,3-dimethyl-7-(2-(methylsulphonyl)ethyl)benzofuran are obtained in the form of an oil. 7.18 g (26 mmol) of 2,3-dimethyl-7-(2-(methylsulphonyl)ethyl)benzofuran and 200 ml of diethylamine are introduced into a 500 ml round-bottomed flask equipped with a reflux condenser. The reaction mixture is stirred for 16 h at reflux and concentrated under vacuum and the residue is purified by silica column chromatography (elution solvent: 9/1 dichloromethane/methanol).

Workup

  1. customto return to 0° C
  2. extractionextraction
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-857aeb68379a453884d7fd03fc62dd16
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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