Hydrochloric Acid → HCID 18957477, compound

HRID 2379571Notes

Reaction equation

HRID 2379571 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.C([Li])CCC.C([O:24][C:25]1[CH2:29][CH2:28][C:27](=O)[CH:26]=1)(C)C.Cl>O1CCCC1.O>[CH:11]1([O:10][C:4]2[CH:3]=[C:2]([C:27]3[CH2:28][CH2:29][C:25](=[O:24])[CH:26]=3)[CH:7]=[CH:6][C:5]=2[O:8][CH3:9])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzeneHCID 189574803-(1-Methylethoxy)-2-cyclopenten-1-oneHCID 178418339Butyllithium

Product 1

HCID 18957477HCID 18957477, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-bromo-2-cyclopentyloxy-1-methoxybenzene (preparation 4) (9.50 g, 35.0 mmol) in tetrahydrofuran (70 ml) at -78° C. under an argon atmosphere was added dropwise n-butyllithium (15 ml of 2.5M solution, 37.5 mmol). The resulting mixture was stirred at -78° C. for 1.25 hr and added dropwise to a cooled solution (0° C.) of 3-isopropoxy-2-cyclopentenone (4.95 g, 35.3 mmol) in tetrahydrofuran (20 ml). Upon completion of the addition, the reaction mixture was allowed to warm to room temperature and was stirred for 1.5 hr. Hydrochloric acid (70 ml of 0.6N solution) was added to the reaction mixture and stirring was continued for 2.5 hr. The reaction mixture was poured into water and extracted with methylene chloride (four times). The combined organic extracts were dried (magnesium sulfate), the solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 1:4:5 methylene chloride/ether/hexanes. Recrystallization from methylene chloride/ether/hexanes provided needles (5.5 g, 63%): m.p. 136°-137° C. Analysis:

Workup

  1. additionUpon completion of the addition
  2. temperatureto warm to room temperature
  3. stirringwas stirred for 1.5 hr
  4. stirringstirring
  5. waitwas continued for 2.5 hr
  6. extractionextracted with methylene chloride (four times)
  7. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  8. customthe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography
  10. washeluting with 1:4:5 methylene chloride/ether/hexanes
  11. customRecrystallization from methylene chloride/ether/hexanes provided needles (5.5 g, 63%)

Sources & evidence

ORD record
ord-4ef10986ae2e44919ff74965a1a27c62
Source dataset
uspto-grants-1994_11
Patent number
US05362915

Reaction notes

Loading…