Tetrahydrofuran → HCID 57290718, compound

HRID 980221Notes

Reaction equation

HRID 980221 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[CH2:10][CH3:11])=[CH:5][CH:4]=1.[H-].[Na+].[CH2:15]([CH:17]1[O:19][CH2:18]1)Br.[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[O:19]1[CH2:18][CH:17]1[CH2:15][CH:22]([C:21]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:23][CH2:24][O:20][CH2:11][CH2:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:15][CH:17]1[O:19][CH2:18]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 92218Benzenemethanol, .alpha.-ethyl-4-methoxy-

Product 1

HCID 57290718HCID 57290718, compound

Conditions

Temperature
60 °C

Procedure

4-Methoxyphenylpropanol (15 g, 0.090M) was added dropwise to a stirred slurry of sodium hydride (4.0 g of a 60% dispersion in oil, 0.10M) in dry tetrahydrofuran (100 ml) and the stirred mixture was heated at 60° C. for 1 hour under a gentle stream of dry nitrogen. On cooling, epibromohydrin (12.8 g 0.0934M) was added and the mixture was stirred at ambient temperature for 65 hours. The solvent was evaporated off under reduced pressure and the residue was treated with water (800 ml) and extracted with dichloromethane. The combined extracts were dried (Na2SO4) and the solvent was evaporated off under reduced pressure to give the crdue product which was further purified by chromotography (silica gel, dichloromethane) to give 2,3-epoxypropyl-4-methoxyphenylpropyl ether as a colourless oil.

Workup

  1. temperatureOn cooling
  2. customThe solvent was evaporated off under reduced pressure
  3. additionthe residue was treated with water (800 ml)
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customthe solvent was evaporated off under reduced pressure
  7. customto give the crdue product which
  8. customwas further purified by chromotography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-a9fe0ca2f6b54bbd8ce317dd6fa6c7f6
Source dataset
uspto-grants-1987_01
Patent number
US04636518

Reaction notes

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