Tetrahydrofuran → HCID 23373020, compound

HRID 1898968Notes

Reaction equation

HRID 1898968 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([Li])CCC.[CH3:21][C:22]1([CH3:29])[CH2:27][CH2:26][C:25](=O)[CH:24]=[CH:23]1.[Cl-].[NH4+].[O:32]1CCCC1>C(O)(C)C>[CH3:21][C:22]1([CH3:29])[C:27](=[O:32])[CH:26]=[C:25]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:24][CH2:23]1

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 23373020HCID 23373020, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-78 °C

Procedure

4-Bromophenol benzyl ether (3.34 g) was dissolved in tetrahydrofuran (20 ml), and the resulting solution was stirred at -78° C. in an argon gas stream. n-Butyllithium (8.33 ml, 1.6 mole solution) was added slowly and the mixture was allowed to stand for 15 minutes. A solution of 4,4-dimethyl-2-cyclohexene-1-one (1.57 g) in tetrahydrofuran (5 ml) was slowly added to the above solution, and then, the resulting mixture was allowed to stand for 30 minutes. Thereafter, a saturated aqueous solution of ammonium chloride was added, the mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated. Acetone (10 ml) was added to the residue. Then, the Jone's reagent previously prepared was added until its color was no longer changed (until it no longer became green). After 30 minutes, the reaction was ceased by adding isopropyl alcohol. The whole was poured into ice water, and the crude product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated. The residue was purified by column chromatography (50 g of SiO2, 5% ethyl acetate/hexane) to obtain the above-titled compound [V-3] (700 mg).

Workup

  1. waitto stand for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated
  5. additionAcetone (10 ml) was added to the residue
  6. customThen, the Jone's reagent previously prepared
  7. additionwas added until its color
  8. waitAfter 30 minutes
  9. extractionthe crude product was extracted with ethyl acetate
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. customthe solvent was evaporated
  12. customThe residue was purified by column chromatography (50 g of SiO2, 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5ba3beb295394faeadf4d4e53f09cbc9
Source dataset
uspto-grants-1996_11
Patent number
US05571831

Reaction notes

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