Potassium Carbonate → HCID 66974008, compound

HRID 2406845Notes

Reaction equation

HRID 2406845 reaction equation
[CH2:1]([C:4]1[C:5]([OH:13])=[CH:6][C:7]2[O:11][CH2:10][CH2:9][C:8]=2[CH:12]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]#[C:23][CH3:24]>CC(C)=O>[CH2:21]([O:13][C:5]1[C:4]([CH2:1][CH2:2][CH3:3])=[CH:12][C:8]2[CH2:9][CH2:10][O:11][C:7]=2[CH:6]=1)[C:22]#[C:23][CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 66973890HCID 66973890, compound

Product 1

HCID 66974008HCID 66974008, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the same procedure as in Example 3 c), a mixture of 5.0 g (0.026 moles) of 5-propyl-6-hydroxy-2,3-dihydrobenzofuran (title 93.5%), 3.9 g (0.028 moles) of anhydrous potassium carbonate in ml 30 of acetone was added with 3.7 g (0.028 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 3/1 (v/v)). A liquid product (3.8 g, purity 96%) was obtained, whose NMR and MS analyses corresponded to those of the aforementioned compound.

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 3/1 (v/v))
  7. customA liquid product (3.8 g, purity 96%) was obtained

Sources & evidence

ORD record
ord-3241e07ae098472a848d2ea2b74153bc
Source dataset
uspto-grants-2014_08
Patent number
US08809389B2

Reaction notes

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