Diethyl Ether → HCID 178439100, compound

HRID 234157Notes

Reaction equation

HRID 234157 reaction equation
[CH:1]([C:3]1[C:9](=[O:10])[C:8]([OH:11])=[CH:7][C:6]([CH:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1)=[O:2].C[Li].[CH3:17]COCC>O1CCCC1>[OH:2][CH:1]([C:3]1[C:9](=[O:10])[C:8]([OH:11])=[CH:7][C:6]([CH:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1)[CH3:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 178418348HCID 178418348, compoundHCID 178439169HCID 178439169, compound

Product 1

HCID 178439100HCID 178439100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

7-formyl-4-isopropyl-2-hydroxy-2,4,6-cycloheptatrien-1-one (2.00 g, 10 mmol) was dissolved in tetrahydrofuran (20 ml) and cooled to -78° C. in a dry ice/acetone bath. A solution of methyllithium the ether (1.4M, 15 ml) was added dropwise to the solution, then dry ice/acetone bath was removed and stirring was continued until the insolubles were dissolved. An aqueous saturated ammonium chloride was added to the reaction mixture and extracted with methylene chloride. The methylene chloride layer was washed with water, dried over anhydrous sodium sulfate and solvent was distilled off to give 2.18 g of 7-(α-hydroxyethyl)-4-isopropyl-2-hydroxy-2,4,6-cycloheptatrien-l-one as a reddish brown oil (yield: quantitative).

Workup

  1. customdry ice/acetone bath was removed
  2. dissolutionwere dissolved
  3. additionAn aqueous saturated ammonium chloride was added to the reaction mixture
  4. extractionextracted with methylene chloride
  5. washThe methylene chloride layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate and solvent
  7. distillationwas distilled off

Sources & evidence

ORD record
ord-c4a0a44a75d0409cbfac10a34001103f
Source dataset
uspto-grants-1997_01
Patent number
US05594144

Reaction notes

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