반응 #93022

반응 방정식

2-(4-chlorophenoxy)-N,N-dimethyl acetamide

di-isopropylamine

ammonium chloride

cyclohexanone

n-butyl lithium

→

Lithium di-isopropylamide

1-[(4-chlorophenoxy)((dimethylamino)carbonyl)methyl]cyclohexanol

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for 20 minutes at -78° C.
2. 2
   workup.WAITAfter 45 minutes at -78° C.
3. 3
   기타The phases were separated
4. 4
   세척the organic layer washed with brine
5. 5
   건조dried over anhydrous potassium carbonate
6. 6
   기타evaporated

실험 절차

Lithium di-isopropylamide was prepared by dissolving di-isopropylamine (11 ml) in tetrahydrofuran (150 ml) followed by the addition of n-butyl lithium (50 ml of 1.7 molar). After 10 minutes stirring, the straw colored liquid was cooled to -78° C. and a solution of 2-(4-chlorophenoxy)-N,N-dimethyl acetamide (16 g, 0.074 mole) in tetrahydrofuran (25 ml) was slowly added. The mixture was stirred for 20 minutes at -78° C. and cyclohexanone (7 ml) added. After 45 minutes at -78° C., the reaction mixture was poured into saturated ammonium chloride solution and a red color ensued. The phases were separated and the organic layer washed with brine, dried over anhydrous potassium carbonate and evaporated giving 1-[(4-chlorophenoxy)((dimethylamino)carbonyl)methyl]cyclohexanol as a red solid. Repeated washing with a cold hexane-isopropanol mixture yielded 2.7 g of a white crystalline solid. Yield: 2.7 g, m.p. 109°-111° C.

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