Cyclohexanone → HCID 780741, compound

HRID 1584645Notes

Reaction equation

HRID 1584645 reaction equation
[N:1]1([CH2:6][C:7]#[CH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[C:14]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>O1CCCC1>[N:1]1([CH2:6][C:7]#[C:8][C:14]2([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 2996161-(Prop-2-yn-1-yl)pyrrolidineHCID 178418339Butyllithium

Product 1

HCID 780741HCID 780741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 1-(pyrrolidin-1-yl)-prop-2-yne (prepared by the method of Biel and DiPierro J. Am. Chem. Soc. 1958, 80, 4609) (0.545 g) in dry tetrahydrofuran (15 ml) was treated at -78° C. with a solution of n-butyl lithium in hexanes (2.5 M, 2.2 ml) and the mixture was allowed to stir at -78° C. for 30 minutes and them permitted to warm to room temperature over the course of one hour. Upon recooling to -78° C. this mixture was treated with a solution of cyclohexanone (0.61 g) in tetrahydrofuran (1 ml). The reaction was permitted to warm to room temperature over the course of two hours, and was then partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, and the pooled organic phase was washed with water, brine, and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give a crude product, which was purified by column chromatography over silica gel (5% methanol in dichloromethane was used as the eluant) to afford the product as a white solid. MS(+ES), m/z: 208 (M+H)+.

Workup

  1. temperatureto warm to room temperature over the course of one hour
  2. customUpon recooling to -78° C.
  3. temperatureto warm to room temperature over the course of two hours
  4. customwas then partitioned between ethyl acetate and water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe pooled organic phase was washed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customto give a crude product, which
  10. customwas purified by column chromatography over silica gel (5% methanol in dichloromethane

Sources & evidence

ORD record
ord-649e8d2efa2240afad0a746aa46a2bfb
Source dataset
uspto-grants-1999_08
Patent number
US05932745

Reaction notes

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