Water → HCID 9833973, compound

HRID 527507Notes

Reaction equation

HRID 527507 reaction equation
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][OH:9].Br[CH2:11][C:12]#[CH:13].O>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:13]([O:9][CH2:8][C:4]1[O:3][CH:7]=[CH:6][CH:5]=1)[C:12]#[CH:11]

Participants

7

Reactant 4

HCID 962WaterHCID 7361Furfuryl AlcoholHCID 7842Propargyl bromideHCID 24758Sodium hydride

Product 1

HCID 9833973HCID 9833973, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (1.570 g, 39.2 mmol) in DMF (46 ml) stirred under argon at 0° C. was dropped a solution of 2-furanylmethanol (3.5 g, 35.7 mmol) in DMF (4 ml) in 20 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. 3-bromo-1-propyne (4.24 g, 35.7 mmol) 80% in toluene was dropped in 10 minutes at 0° C., then the mixture was left stirring at room temperature overnight. Water was added and then the mixture was extracted with ethyl ether 3 times. The organic phase was dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography on silica (Biotage SP1 instrument), eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15. Evaporation afforded the title compound (1.63 g).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 15 minutes
  2. waitthe mixture was left
  3. stirringstirring at room temperature overnight
  4. extractionthe mixture was extracted with ethyl ether 3 times
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography on silica (Biotage SP1 instrument)
  8. washeluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15
  9. customEvaporation

Sources & evidence

ORD record
ord-4efd8e0af83c48e0971fc9d1eb77c3cc
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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