Triethylamine → HCID 67168649, compound

HRID 1506317

Reaction equation

HRID 1506317 reaction equation
[C:1]([C:3]1([CH3:6])[CH2:5][CH2:4]1)#[CH:2].Cl/[C:8](=[N:14]\[OH:15])/[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C>C(OCC)C>[CH2:12]([O:11][C:9]([C:8]1[CH:2]=[C:1]([C:3]2([CH3:6])[CH2:5][CH2:4]2)[O:15][N:14]=1)=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95760052-Chloro-2-hydroxyiminoacetic acid ethyl esterHCID 215905601-Ethynyl-1-methylcyclopropane

Product 1

HCID 67168649HCID 67168649, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 1-ethynyl-1-methylcyclopropane (Preparation 4B, 5.0 g, 62.4 mmol) and (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (4.73 g, 31.2 mmol) in diethyl ether (80 mL) was added a solution of triethylamine (8.67 mL, 62.4 mmol) in diethyl ether (20 mL) dropwise over 75 min. After complete addition, the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash silica gel chromatography using a 10% mixture of ethyl acetate in hexane to give ethyl-5-(1-methylcyclopropyl)isoxazole-3-carboxylate (3.54 g, 65% yield) as a yellow liquid. The product had an HPLC ret. time=2.23 min.-(condition B); LC/MS M+1=196.07. 1H NMR (400 MHz, CDCl3) δ ppm 0.79 (m, 2H), 1.13 (m, 2H), 1.26 (t, J=7.15 Hz, 3H), 1.35 (s, 3H), 4.31 (q, J=7.12 Hz, 2H), and 6.23 (s, 1H).

Workup

  1. additionAfter complete addition
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-d720e293ef4a49239d4156d3db03cc95
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Linked notes

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