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

HRID 350734노트

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HRID 350734 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5bf2fb238e694f07a69c5b47b3e922ee
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183276B2

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