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ChemicalBook CAS DataBase List 2-(tert-Bytyl)-5-(1-methylethylidene)-1,3-cyclopentadiene
132380-73-5

2-(tert-Bytyl)-5-(1-methylethylidene)-1,3-cyclopentadiene synthesis

4synthesis methods
-

Yield:132380-73-5 95%

Reaction Conditions:

with n-butyllithium in tetrahydrofuran;hexane;water;acetone;

Steps:

6.1 (1)

(1) Synthesis of 3-tert-butyl-6,6-dimethylfulvene To a solution of 1.53 g (13 mmol) of tert-butylcyclopentadiene in 30 ml of THF, 9.0 ml (14 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 1.7 ml (16 mmol) of acetone was further added at -78°C, followed by stirring at room temperature for 2 days. To the reaction solution, water was added. After extraction with ether, the solvent was distilled off, and the residue was subjected to column chromatography (silica gel, developing solvent: hexane) to obtain 2.00 g of a yellow liquid (yield: 95 %). The analyzed values are given below. 1H-NMR (270 MHz, in CDCl3, Based on TMS): δ6.53 (d, 2H), 6.14 (t, 1H), 2.16 (s, 3H), 2.14 (s, 3H), 1.20 (s, 9H)

References:

EP1138687,2001,A1