Hydrochloric Acid → 3-Phenyl-5-(2-phenylethyl)isoxazole-4-carboxylic acid

HRID 1840303

반응식

HRID 1840303 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=[O:14].[Li].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O1CCCC1.CCCCCC.O>[C:7]1([C:4]2[C:3]([C:13]([OH:15])=[O:14])=[C:2]([CH2:1][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:6][N:5]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 3028194Lithium

생성물 1

HCID 234479063-Phenyl-5-(2-phenylethyl)isoxazole-4-carboxylic acid수율 84%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 1.5 g of 5-methyl-3-phenyl-4-isoxazolecarboxylic acid in 50 mL of anhydrous tetrahydrofuran stirred at −78° C. under N2 atmosphere, 5.9 mL of a 2.5M solution of n-buthyl lithium in n-hexane was added and the solution was stirred at −78° C. for 2 hours. Afterwards, 0.89 mL of benzyl bromide was added at −78° C. and the solution stirred at room temperature for 2 hours. After overnight resting, the solution was poured into water (300 mL), acidified with hydrochloric acid and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water, dried (sodium sulphate) and the solvents were evaporated to dryness. The solid residue was washed with petroleum ether to give 1.82 g (84%) of the title compound as an amorphous solid.

후처리

  1. stirringthe solution stirred at room temperature for 2 hours
  2. waitAfter overnight resting
  3. extractionextracted with ethyl acetate (2×200 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (sodium sulphate)
  6. customthe solvents were evaporated to dryness
  7. washThe solid residue was washed with petroleum ether

출처 및 근거

ORD 기록
ord-78b2f2ba443a4c5b8c168a26730894c8
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680319B2

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