Hydrochloric Acid → HCID 21465100, compound

HRID 1939887Notes

Reaction equation

HRID 1939887 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]23[CH2:16][CH2:15][CH:12]([CH2:13][CH2:14]2)[C:11](=[O:17])[O:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:19][CH2:20]O>O>[C:1]1([CH2:7][CH2:8][C:9]2[CH2:16][CH2:15][CH:12]([C:11]([O:10][CH2:19][CH3:20])=[O:17])[CH2:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 21465089HCID 21465089, compound

Product 1

HCID 21465100HCID 21465100, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Slowly add 2-phenylethyl bromide (2.6 g) to a slurry of Mg (0.37 g) in THF (50 mL) and heat at reflux for 4 h. Cool the solution to ambient temperature and add to a solution of ethyl 4-oxo-cyclo-hexanecarboxylate (2.4 g) in THF (50 mL). After 2 h, pour the reaction mixture into a half-saturated solution of NH4Cl and extract with EtOAc. Partially purify the product on a silica gel column, eluting with EtOAc. Dissolve the product in toluene (100 mL), treat with p-TsOH and heat at reflux overnight with azeotropic removal of water. Cool the reaction mixture, wash with saturated NaHCO3 solution and concentrate. Purify the crude product on a silica gel column, eluting with CH2Cl2 to obtain ethyl 4-(2-phenylethyl)-cyclohex-3-enecarboxylate (0.45 g) and 1-(2-phenyl-ethyl)-2-oxabicyclo[2.2.2]octan-3-one (0.71 g). Dissolve 1-(2-phenyl-ethyl)-2-oxabicyclo[2.2.2]octan-3-one in EtOH, treat with conc.HCl (catalytic) and heat at reflux overnight. Dilute the reaction mixture with water and extract with EtOAc. Concentrate the organic layer to obtain additional ethyl 4-(2-phenylethyl)-cyclohex-3-enecarboxylate (0.88 g).

Workup

  1. temperatureat reflux overnight
  2. extractionextract with EtOAc
  3. concentrationConcentrate the organic layer

Sources & evidence

ORD record
ord-3ac980b8dc24482085dee910bd6721b3
Source dataset
uspto-grants-1997_12
Patent number
US05698548

Reaction notes

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