Potassium Carbonate → 5-(But-2-ynyloxy)-2,3-dihydrobenzofuran

HRID 2406843Notes

Reaction equation

HRID 2406843 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]#[C:20][CH3:21]>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1)[C:19]#[C:20][CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 111263112,3-Dihydro-5-hydroxybenzo(b)furan

Product 1

HCID 669740095-(But-2-ynyloxy)-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the same procedure as in Example 2), a mixture of 4.0 g (0.029 moles) of 5-hydroxy-2,3-dihydrobenzofuran, 4.0 g (0.029 moles) of anhydrous potassium carbonate in ml 25 of acetone was added with 3.9 g (0.029 moles) of 1-bromo-2-butyne. The mixture was heated to reflux for 6 hrs. After cooling to room temperature, the mixture was filtered and the filtrate evaporated u.v (20° C./ 21 mbar). The residue so obtained was purified by chromatography on silica column (eluant n-hexane/ethyl acetate 5/1 (v/v))

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hrs
  3. filtrationthe mixture was filtered
  4. customthe filtrate evaporated u.v (20° C./ 21 mbar)
  5. customThe residue so obtained
  6. customwas purified by chromatography on silica column (eluant n-hexane/ethyl acetate 5/1 (v/v))

Sources & evidence

ORD record
ord-b87f0527001842439aeddc85161ef60c
Source dataset
uspto-grants-2014_08
Patent number
US08809389B2

Reaction notes

Loading…