Diethyl Ether → HCID 11007470, compound

HRID 1110016Notes

Reaction equation

HRID 1110016 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11]1([Li])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1CCCCC1.C(OCC)C>O1CCCC1.O>[C:11]1([CH:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:1]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7047QuinolineHCID 8078CyclohexaneHCID 178506676HCID 178506676, compound

Product 1

HCID 11007470HCID 11007470, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2 °C

Procedure

30 g of quinoline were dissolved in 100 ml tetrahydrofuran. The solution was cooled to 2° C., then 19.6 g of phenyllithium in the form of a 2M solution in a 70:30 mixture of cyclohexane and diethyl ether were added over the course of 2 hours while the temperature was maintained between 0° and 2° C. The reaction mixture was then allowed to warm to room temperature. To work up the reaction mixture it was added to water and then extracted with diethyl ether. The ether phase was washed with water until neutral, dried and concentrated. 50 g of crude product were obtained, which was purified by chromatography on a silica gel column using toluene as the eluent. 20.3 g of 1,2-dihydro-2-phenylquinoline having a melting point of 75° C. were obtained.

Workup

  1. additionwere added over the course of 2 hours while the temperature
  2. temperaturewas maintained between 0° and 2° C
  3. temperatureto warm to room temperature
  4. extractionextracted with diethyl ether
  5. washThe ether phase was washed with water until neutral,
  6. customdried
  7. concentrationconcentrated
  8. custom50 g of crude product were obtained
  9. customwhich was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-b4a08e3a46b6449f98eaa4564d8fdb5b
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

Loading…