ChemicalBook CAS DataBase List Lithium tert-butoxide

Lithium tert-butoxide synthesis

12synthesis methods

Product Name:Lithium tert-butoxide
CAS Number:1907-33-1
Molecular formula:C4H9LiO
Molecular Weight:80.05

75-65-0 Synthesis

75-65-0
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$10.00/10ml

1907-33-1
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$23.80/2g

Yield:-

Reaction Conditions:

with n-butyllithium

Steps:

5 Example 5; Preparation of methyl 3 (R)-3- (4- trifluoromethylphenylamino) pentanoylcarbamate

In an atmosphere of nitrogen, 3 (R)-3- (4- TRIFLUOROMETHYLPHENYLAMINO)-2-PENTANAMIDE (3. 0g, 11. 5MMOL) and methyl chlorocarbonate (1.35g, 14.3 mmol) were mixed in 15 ml of diisopropyl ether, and the mixture was stirred under cooling with ice. To this solution, a THF-hexane solution of lithium tert-butoxide prepared from 1.6-M n- butyllithium (15.2 ml, 24.3 mmol) and tert-butanol (1.8g, 24. 3MMOL) was added dropwise at the temperature of not more than 5 C. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes. Then, the reaction was quenched with 1M hydrochloric acid. The organic layer was separated, washed successively with a saturated solution of sodium chloride and water. The solvent was then removed by evaporation to give 3.41g of the title compound. The yield was 93%. Optical purity: 96% e. e. 1H-NMR (acetone-d6, 8PPM) : 9.36 (bs, 1H), 7.37 (d, J=8.6Hz, 2H), 6.77 (d, J=8.6Hz, 2H), 5.46 (bd, J=8.9Hz, 1H), 4.00-3. 93 (m, 1H), 3.69 (s, 3H), 2.96 (dd, J=6. 2Hz, 16.2Hz, 1H), 2.86 (dd, J=6.3Hz, 16. 1HZ, 1H), 1.77-1. 68 (m, 1H), 1.66-1. 57 (m, 1H), 0.97 (t, J=7.5Hz, 3H).

References:

WO2004/74255,2004,A2 Location in patent:Page 77

29786-93-4 Synthesis