Water → HCID 12971154, compound

One equivalent of n-butyl lithium was added to a solution in which 7.038 g (34.3 mmol) of 2-bromo-3-methoxy-1,3-dimethyl-cyclopentene compound prepared in the example 3 was dissolved in 38 ml of ether at −25° C. nitrogen atmosphere. When white solid was precipitated, the temperature was elevated to 10° C. and the reaction was continued for further 10 minutes. The temperature was lowered to −25° C. and the fulvene compound prepared in the example 2 was added. Completion of reaction is determined by the development of yellow color of the reaction mixture. 50 ml of water was added to the reaction mixture and the solvent was removed using the rotatory evaporator. 50 ml of 2N HCl solution was added to the organic layer extracted with 50 ml of ethyl acetate, and the resulting mixture was vigorously shaked for 2 minutes. Water layer was removed by layer separation and the organic layer was neutralized with 50 ml of a saturated sodium bicarbonate solution. Isolated organic layer was dried over magnesium sulfate, and then the vacuum distillation was preformed to give 4.17 g of yellow 2,2′-methylenebis(1,3-dimethyl-1,3-cyclopentadiene) compound. Yield: 61%.

1. customprepared in the example 3
2. customWhen white solid was precipitated
3. customwas elevated to 10° C.
4. customwas lowered to −25° C.
5. customthe fulvene compound prepared in the example 2
6. additionwas added
7. customCompletion of reaction
8. customthe solvent was removed
9. customthe rotatory evaporator
10. addition50 ml of 2N HCl solution was added to the organic layer
11. extractionextracted with 50 ml of ethyl acetate
12. waitthe resulting mixture was vigorously shaked for 2 minutes
13. customWater layer was removed by layer separation
14. dry with materialIsolated organic layer was dried over magnesium sulfate
15. distillationthe vacuum distillation

ORD record

ord-53eb16a11b234efa9612fcd25db892e5

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166731B2