Cyclohexylisopropylamine → Lithium cyclohexylisopropylamide

HRID 1196565Notes

Reaction equation

HRID 1196565 reaction equation
C([Li:5])CCC.[CH:6]([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:8])[CH3:7].C[Si](CC(OCC)=O)(C)C.N1C2C(=CC=CC=2)C=CC=1OCCCCCCCCCC(=O)C>C1COCC1>[CH:6]([N-:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:8])[CH3:7].[Li+:5]

Participants

6

Reactant 4

HCID 62386CyclohexylisopropylamineHCID 77687Ethyl trimethylsilylacetateHCID 19898708HCID 19898708, compoundHCID 178418339Butyllithium

Product 1

HCID 10877271Lithium cyclohexylisopropylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium N-isopropyl-N-cyclohexylamide was prepared at -78° in anydrous THF from n-butyl lithium (6.1 mmol) and N-isopropyl-N-cyclohexylamine (1.00 ml). Ethyl trimethylsilylacetate (1.1 ml) was added, followed after 10 minutes by addition of the above ketone in THF. The reaction mixture was left at room temperature for 16 hours and worked-up in the usual manner. Excess ethyl trimethylsilylacetate was removed in vacuo and purification by column chromatography on silica (9:1, hexane: ether) gave (2E/Z)ethyl 3-methyl-12-(2-quinolinyloxy)dodec-2-enoate (0.33 g). This was converted to the title compound by analogy with Stages c and d of EXAMPLE I.

Workup

  1. customExcess ethyl trimethylsilylacetate was removed in vacuo and purification by column chromatography on silica (9:1, hexane: ether)

Sources & evidence

ORD record
ord-b08c390ea1b44ac19d1543e3a2b99ae8
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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