Triethylamine → HCID 67168649, 화합물

HRID 1506317

반응식

HRID 1506317 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 67168649HCID 67168649, 화합물수율 65%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d720e293ef4a49239d4156d3db03cc95
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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