Water → HCID 9833973, compound

HRID 716822Notes

Reaction equation

HRID 716822 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 35%

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. a solution of 2-furanylmethanol (3.5 g, 35.7 mmol) in DMF (4 ml) was added dropwise over 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 gel (Biotage SP1 instrument), eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15. Evaporation afforded the title compound (1.63 g, 35% yield).

Workup

  1. additionwas added dropwise over 20 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 gel (Biotage SP1 instrument)
  8. washeluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15
  9. customEvaporation

Sources & evidence

ORD record
ord-af4a48e782374f1c92c1df4161878677
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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