Triethylamine → 3-Ethoxy-2-hexyl-4,4-dimethylcyclobut-2-en-1-one

HRID 1815041Notes

Reaction equation

HRID 1815041 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH:9]([CH3:11])[CH3:10].[CH2:14]([O:16][C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:15]>C(OCC)C>[CH2:14]([O:16][C:17]1[C:9]([CH3:11])([CH3:10])[C:8](=[O:12])[C:18]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 108773451-ethoxy-1-octyne

Product 1

HCID 219195633-Ethoxy-2-hexyl-4,4-dimethylcyclobut-2-en-1-oneYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared using a modification of the method of Wasserman, H. H. et al, [J. Org. Chem, 38, 1451-1455, (1973)]; triethylamine (22 ml) was added dropwise at room temperature to a well-stirred solution of isobutyryl chloride (7.3 ml, 69 mmol) and 1-ethoxy-1-octyne [prepared according to the method of Kocienski, P. et al. Tetrahedron Lett. 1833, 30, (1989)] (6.5 g, 63 mmol) in diethylether (100 ml). The reaction was warmed to 35° and stirred for 96 h prior to cooling and filtration. The filtrate was concentrated in vacuo and the residual oil chromatographed (SiO2; hexanes 80:EtOAc 20) to give the title compound as a brown oil (8.6 g, 38 mmol, 61%). δH (CDCl3, 300K) 4.34 (2H, d, J 7.1 Hz), 2.05 (2H, dd, J 5.6 Hz, 7.3 Hz), 1.44 (3H, t, J 7.1 Hz), 1.27-1.12 (8H, m), 1.23 (6H, s), 0.89 (3H, t, J 2.7 Hz). m/z (ES+, 70V) 225.0 (MH+).

Workup

  1. customThe title compound was prepared
  2. customprepared
  3. temperatureThe reaction was warmed to 35°
  4. temperatureto cooling
  5. filtrationfiltration
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residual oil chromatographed (SiO2; hexanes 80:EtOAc 20)

Sources & evidence

ORD record
ord-9a7aaf0d54904fc6b32c1b889df8785a
Source dataset
uspto-grants-2005_04
Patent number
US06878718B2

Reaction notes

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