Tetrahydrofuran → HCID 67331211, compound

HRID 2408256Notes

Reaction equation

HRID 2408256 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10]([Mg]Br)[CH:11]=[CH2:12].C1COCC1>>[CH3:12][C:11](=[CH2:10])[CH:5]([C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([CH3:1])[CH:3]=1)[OH:6]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 121053-MethylbenzaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 67331211HCID 67331211, compoundYield 51%

Conditions

Temperature
0 °C

Procedure

3-Methylbenzaldehyde (Aldrich 97%, 62 g, 0.5 mol) was added drop-wise over 1 hour to a commercial solution of 2-propenyl magnesium bromide in THF (Aldrich 0.5 N, 800 ml, 0.4 mol), at −78° C. under nitrogen. The cooling bath was removed and the reaction stirred for 5 hours, before being cooled to 0° C. A saturated aqueous solution of ammonium chloride (300 ml) was added drop-wise at such a rate that the temperature was kept below 20° C. Diethyl ether (600 ml) was then added and the reaction was transferred to a separating funnel. After shaking vigorously, the phases were separated. The organic phase was washed with water and saturated aqueous sodium bicarbonate. Each aqueous phase was re-extracted with diethyl ether. The organic fractions were combined and dried over solid anhydrous sodium sulfate. The solid was filtered off, rinsed with diethyl ether and the solvents were removed under vacuum. The product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 5:1) followed by distillation through a 20-cm Widmer column. 33 g of the desired product were obtained (yield=51%). B.P.=55° C./0.009 mbar

Workup

  1. customat −78° C.
  2. customThe cooling bath was removed
  3. additionA saturated aqueous solution of ammonium chloride (300 ml) was added drop-wise at such a rate that the temperature
  4. customwas kept below 20° C
  5. additionDiethyl ether (600 ml) was then added
  6. customthe reaction was transferred to a separating funnel
  7. stirringAfter shaking vigorously
  8. customthe phases were separated
  9. washThe organic phase was washed with water and saturated aqueous sodium bicarbonate
  10. extractionEach aqueous phase was re-extracted with diethyl ether
  11. dry with materialdried over solid anhydrous sodium sulfate
  12. filtrationThe solid was filtered off
  13. washrinsed with diethyl ether
  14. customthe solvents were removed under vacuum
  15. customThe product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 5:1)
  16. distillationfollowed by distillation through a 20-cm Widmer column

Sources & evidence

ORD record
ord-d72a286f05924888a4481b4e54438ec6
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

Loading…