Triethylamine → 3-Ethoxy-4,4-dipropyl-2-cyclobuten-1-one

HRID 491547Notes

Reaction equation

HRID 491547 reaction equation
C(N(CC)CC)C.[CH2:8]([CH:11]([CH2:15][CH2:16][CH3:17])[C:12](Cl)=[O:13])[CH2:9][CH3:10].[CH2:18]([O:20][C:21]#[CH:22])[CH3:19]>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:18]1[C:11]([CH2:15][CH2:16][CH3:17])([CH2:8][CH2:9][CH3:10])[C:12](=[O:13])[CH:19]=1)[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61239Ether, ethyl ethynylHCID 762402-Propylvaleryl chloride

Product 1

HCID 219197313-Ethoxy-4,4-dipropyl-2-cyclobuten-1-oneYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 (29 ml) was added dropwise at room temperature to a well-stirred solution of di-n-propylacetyl chloride (13.9 g, 85.8 mmol) and ethyl ethynylether (15 g, 40% solution in hexanes, 85.7 mmol) in toluene (120 ml. The reaction was warmed to 60° and stirred for 48 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 (11.2 g, 57.1 mmol, 67%). δH (CDCl3, 300K) 5.02 (1H, s), 4.32 (2H, q, J 7.1 Hz), 1.69-1.61 (4H, m), 1.45-1.40 (4H, m), 1.02 (6H, t, J 7.3 Hz). m/z (ES+, 70V) 197.1 (MH+).

Workup

  1. customThe title compound was prepared
  2. temperatureThe reaction was warmed to 60°
  3. temperatureto cooling
  4. filtrationfiltration
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residual oil chromatographed (SiO2; hexanes 80: EtOAc 20)

Sources & evidence

ORD record
ord-598bf1c0812f4b51ad6bbc53c5652cce
Source dataset
uspto-grants-2009_05
Patent number
US07531549B2

Reaction notes

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