Hydrochloric Acid → HCID 69292865, compound

HRID 900763Notes

Reaction equation

HRID 900763 reaction equation
[CH3:1][O:2][N-]C.[C:5]1([Mg]Br)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.CCO[CH2:17][CH3:18]>C1COCC1>[CH:18]1([C:1]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[CH2:17][CH2:7][CH:6]=[CH:5][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 53630747Methoxy-methyl amideHCID 178418255HCID 178418255, compound

Product 1

HCID 69292865HCID 69292865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The N-methoxy-N-methyl amide was dissolved in dry THF (10 ml) and cooled down to 0° C. A 3M etheral phenyl magnesium bromide solution (17.5 ml, 52.5 mmol) was added dropwise and then the mixture was heated at 65° C. for 1 hour. The mixture was cooled at room temperature and carefully treated with a 1 N HCl solution for 30 minutes at 40° C. The solution was diluted with ether and the organic phase separated, dried over MgSO4 and concentrated. The residual oil was chromatographied on silica gel (CH2Cl2/hexane 10/90) and the 4-cyclohepten-1-yl(phenyl)methanone 21 was isolated as a colorless oil (1.35 g, 77%).

Workup

  1. temperaturethe mixture was heated at 65° C. for 1 hour
  2. temperatureThe mixture was cooled at room temperature
  3. customthe organic phase separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-719df63e42004abab84bdd29011c9330
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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