Hydrochloric Acid → Ethyl (2-iodobenzoyl)acetate

HRID 986234노트

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HRID 986234 반응식
C1(NC(C)C)CCCCC1.C([Li])CCC.[I:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].Cl.[C:27]([O:30][CH2:31][CH3:32])(=[O:29])[CH3:28]>O1CCCC1.CCCCCC>[I:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([CH2:28][C:27]([O:30][CH2:31][CH3:32])=[O:29])=[O:20]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 62386CyclohexylisopropylamineHCID 691122-Iodobenzoyl chlorideHCID 178418339Butyllithium

생성물 1

HCID 4143714Ethyl (2-iodobenzoyl)acetate수율 71.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

Cyclohexyl isopropylamine (10.6 grams) is dissolved in 80 ml of tetrahydrofuran and the solution is cooled to -78° C. In a nitrogen stream, a solution of n-butyl lithium (about 15%) in hexane solution (26 ml) is added thereto, and the mixture temperature is raised to -40° C. Then it is cooled to -78° C. once again, 3.3 grams of ethyl acetate is gradually added thereto and, ten minutes thereafter, a solution of 10 grams of o-iodobenzoyl chloride in tetrahydrofuran is dropped thereinto gradually. The mixture is stirred at -78° C. for one hour, then gradually warmed up to 0° C. within two to three hours, 20 ml of 20% hydrochloric acid solution is added thereto, the mixture is poured into ice water, and extracted with ether. The extract is washed with a saturated aqueous solution of sodium bicarbonate, dried with anhydrous magnesium sulfate, ether is evaporated therefrom, and the resulting oil is purified by distilling in vacuo to give 8.5 grams of pale yellow oil, b.p. 142° C./3 mmHg.

후처리

  1. temperaturethe mixture temperature is raised to -40° C
  2. temperatureThen it is cooled to -78° C. once again
  3. temperaturegradually warmed up to 0° C. within two to three hours
  4. extractionextracted with ether
  5. washThe extract is washed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried with anhydrous magnesium sulfate, ether
  7. customis evaporated
  8. customthe resulting oil is purified
  9. distillationby distilling in vacuo

출처 및 근거

ORD 기록
ord-e28b9372110640a8a75bd3ca316b6df7
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04711898

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