Tetrahydrofuran → HCID 15592215, compound

HRID 2417693Notes

Reaction equation

HRID 2417693 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[CH2:15]([Li])[CH2:16][CH2:17][CH3:18].[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[CH3:13][C:11]1([CH3:14])[CH2:10][O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:21]([OH:20])[CH2:22][CH2:23][CH2:24][CH2:18][CH2:17][CH2:16][CH2:15][CH2:15][CH2:16][CH2:17][CH2:18][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:3][CH:4]=2)=[N:12]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 178418339Butyllithium

Product 1

HCID 15592215HCID 15592215, compound

Procedure

While under an argon atmosphere, a solution of the product of Example 3 (4 mmole) in tetrahydrofuran (100 ml) was cooled with stirring to ca. -75° C. n-Butyllithium (2 ml; 2.04M in hexane) was added dropwise using a syringe over 15 min. After stirring for 2 hours a second solution of octadecyl aldehyde (4 mmole) in tetrahydrofuran (100 ml) precooled to -5° C. was canulated to the above solution over 25 min., maintaining the temperature below -60° C. The reaction was allowed to warm to room temperature over the next 2.5 hours, then was quenched with water (10 ml) and stirred for 60 hours. Most of the tetrahydrafuran was evaporated under a stream of nitrogen. More water (100 ml) was added and the mixture was extracted into ethyl acetate. The combined extracts were dried over sodium sulfate and filtered, then the solvent was removed by a nitrogen stream to give an oil. The product was purified by chromatography on silica gel to give 0.80 g of the title compound, m.p. ca. 72°-75° C.

Workup

  1. additionwas added dropwise
  2. customover 15 min
  3. customprecooled to -5° C.
  4. temperaturemaintaining the temperature below -60° C
  5. customwas quenched with water (10 ml)
  6. customMost of the tetrahydrafuran was evaporated under a stream of nitrogen
  7. additionMore water (100 ml) was added
  8. extractionthe mixture was extracted into ethyl acetate
  9. dry with materialThe combined extracts were dried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was removed by a nitrogen stream
  12. customto give an oil
  13. customThe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3739506142374d8fa0ba29c019d5ec82
Source dataset
uspto-grants-1984_09
Patent number
US04469885

Reaction notes

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