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

HRID 1840303

反応式

HRID 1840303 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-78b2f2ba443a4c5b8c168a26730894c8
出典データセット
uspto-grants-2004_01
特許番号
US06680319B2

関連ノート

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