Carbon Dioxide → [2-Methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl)carboxylic acid

HRID 350734ノート

反応式

HRID 350734 の反応式
Br[C:2]1[O:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]1[CH:17]=[CH:16][C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=1.O1CCCC1.CCCCCC.C([Li])CCC.[C:34](=[O:36])=[O:35]>O>[CH3:7][C:5]1[O:6][C:2]([C:34]([OH:36])=[O:35])=[C:3]([C:8]2[CH:17]=[CH:16][C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[CH:9]=2)[N:4]=1

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 230619435-Bromo-2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazoleHCID 178418244HCID 178418244、化合物

生成物 1

HCID 21088470[2-Methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl)carboxylic acid収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-78 °C

実験手順

To a mixed solution of 5-bromo-2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazole (11.0 g) and tetrahydrofuran (100 mL) was added dropwise a 1.6N n-butyllithium hexane solution (24 mL) at −78° C. under a nitrogen atmosphere. After stirring the reaction mixture at −78° C. for 10 min, CO2 gas was blown into the reaction mixture for 30 min. The reaction mixture was poured into water and washed with ether. The aqueous layer was acidified with conc. hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give [2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]carboxylic acid (7.4 g, yield 76%) as crystals. Recrystallization from ethyl acetate gave colorless crystals. melting point: 183–185° C.

後処理

  1. washwashed with ether
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-5bf2fb238e694f07a69c5b47b3e922ee
出典データセット
uspto-grants-2007_02
特許番号
US07183276B2

反応ノート

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