Diethyl Ether → HCID 21409560, compound

HRID 2071873Notes

Reaction equation

HRID 2071873 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12](Cl)[C:11]([CH3:16])([CH3:15])[C:10]=2[CH:17]=1)(=[O:4])=[O:3].CCOCC.[CH3:23][C:24]([CH3:28])([OH:27])[CH2:25][CH3:26]>>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([O:27][C:24]([CH3:28])([CH3:23])[CH2:25][CH3:26])[C:11]([CH3:16])([CH3:15])[C:10]=2[CH:17]=1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 64052-Methyl-2-butanolHCID 21409554HCID 21409554, compound

Product 1

HCID 21409560HCID 21409560, compoundYield 43%

Procedure

A solution of 2-chloro-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (14g, 0.05 mole) in 1,1-dimethylpropanol (50 ml) was boiled under reflux for 41/2 hours. After cooling, the solution was taken into ether (250 ml), washed with dilute aqueous sodium hydroxide solution (twice) and with water (twice) and dried over sodium sulphate. The solvent was then distilled off under reduced pressure to give 2,3-dihydro-3,3-dimethyl-2-(1,1-dimethylpropoxy)benzofuran-5-yl methanesulphonate (7g, 43% yield) as a pale yellow oil.

Workup

  1. temperatureunder reflux for 41/2 hours
  2. temperatureAfter cooling
  3. washwashed with dilute aqueous sodium hydroxide solution (twice) and with water (twice) and
  4. dry with materialdried over sodium sulphate
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-d7c0a8f7bb4449779611f8441364c2f1
Source dataset
uspto-grants-1977_09
Patent number
US04049420

Reaction notes

Loading…