Isopropanol → HCID 23373018, compound

HRID 1720898Notes

Reaction equation

HRID 1720898 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1([CH3:17])[CH2:15][CH2:14][C:13](=O)[CH:12]=[CH:11]1.[Cl-].[NH4+].C([OH:23])(C)C>O1CCCC1>[CH3:9][C:10]1([CH3:17])[CH2:15][CH2:14][C:13]([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=2)=[CH:12][C:11]1=[O:23]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-

Product 1

HCID 23373018HCID 23373018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1-bromo-4-fluorobenzene (7.06 g, 40 mmole) was dissolved in 20 ml of tetrahydrofuran, then the resulting solution was stirred at -78° C. in an argon gas stream. N-butyl lithium (25.2 ml, 1.6 mole solution) was added slowly and the solution was allowed to stand for 15 minutes. A solution of 5 g (40 mmole) of 4,4-dimethyl-2-cyclohexene-1-one in 20 ml of tetrahydrofuran was slowly added to the above solution, and then, the resulting solution was allowed to stand for 30 minutes. Thereafter, a saturated aqueous solution of ammonium chloride was added, the whole solution was poured into ice water, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate to remove the solvent. 20 ml of acetone was added to the residue, until the Jone's reagent previously prepared no longer changed color (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 to the solvent was removed by evaporation. The residue was purified by column chromatography (10% ethyl acetate/hexane) to obtain the above-titled compound [V-1] (7.8 g).

Workup

  1. waitto stand for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customto remove the solvent
  5. addition20 ml of acetone was added to the residue, until the Jone's reagent
  6. custompreviously prepared no longer changed color (until it no longer became green)
  7. waitAfter 30 minutes
  8. extractionthe crude product was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried over sodium sulfate to the solvent
  10. customwas removed by evaporation
  11. customThe residue was purified by column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-68a941c9b52f4023a9c4704ccac17dbf
Source dataset
uspto-grants-1996_04
Patent number
US05508298

Reaction notes

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