Water → HCID 19363357, compound

HRID 850483Notes

Reaction equation

HRID 850483 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=2)=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C([Li])CCC.[CH2:27]1[O:29][CH2:28]1.O>C(COC)OC>[CH3:14][C:12]1([CH3:15])[CH2:11][O:10][C:9]([C:6]2[C:5]([CH:28]([OH:29])[CH3:27])=[C:4]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[N:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 6354Ethylene OxideHCID 19363243HCID 19363243, compoundHCID 178418339Butyllithium

Product 1

HCID 19363357HCID 19363357, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-60 °C

Procedure

2-(4-Methoxy-3-pentyloxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (373 mg, 1.28 mmol, 1 eq) was dissolved in dimethoxyethane (7 ml). The solution was cooled to -60° C., and n-butyllithium (1.6M hexane solution)(1.76 ml, 2.82 mmol, 2.2 eq) was added dropwise. The mixture was stirred at said temperature for 1.5 hours. Ethylene oxide was added dropwise, and the mixture was stirred for 1.0 hour. The mixture was heated to room temperature, and further stirred for 2 hours. Water (50 ml) was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate (50 ml). The organic layers were combined, washed with saturated brine (100 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3/1-2/1) to give [6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-3-methoxy-2-pentyloxyphenyl]ethanol (164 mg, 38.2%) as an oil.

Workup

  1. customfor 1.5 hours
  2. stirringthe mixture was stirred for 1.0 hour
  3. temperatureThe mixture was heated to room temperature
  4. stirringfurther stirred for 2 hours
  5. extractionthe mixture was extracted twice with ethyl acetate (50 ml)
  6. washwashed with saturated brine (100 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe drying agent was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3/1-2/1)

Sources & evidence

ORD record
ord-b868da8c304342f4a17d1059ca22c034
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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