Phenyl-t-butylacetylene → Methyl 4-tert-butyl-5-phenylisoxazole-3-carboxylate

HRID 1804469

반응식

HRID 1804469 반응식
[CH3:1][C:2]([CH3:12])([CH3:11])[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N+:13]([CH:16](C(OC)=O)[C:17]([O:19][CH3:20])=[O:18])([O-])=[O:14]>C1(C)C=C(C)C=C(C)C=1>[C:2]([C:3]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[N:13][O:14][C:4]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:12])([CH3:11])[CH3:1]

참가 물질

4

반응물 2

HCID 138165Phenyl-t-butylacetyleneHCID 226085Dimethyl nitromalonate

생성물 1

HCID 58537183Methyl 4-tert-butyl-5-phenylisoxazole-3-carboxylate수율 15.4%

시약·촉매·용매 1

HCID 7947Mesitylene용매

실험 절차

A solution of (3,3-Dimethylbut-1-ynyl)benzene (400 mg, 2.53 mmol) and dimethyl nitromalonate (0.853 mL, 6.32 mmol) in mesitylene (5 mL) was heated at 150° C. for 48 h. The reaction mixture was concentrated, and the residue was purified by silica gel chromatography with hexanes/ethyl acetate (10/1) to yield methyl 4-tert-butyl-5-phenylisoxazole-3-carboxylate (101 mg). The compound had an HPLC ret. time=3.39 min.−Column. YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100. LC-MS: M+1=260+.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel chromatography with hexanes/ethyl acetate (10/1)

출처 및 근거

ORD 기록
ord-8306893196d84c0e85da5b01c4b0e7ec
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354398B2

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