Hydrochloric Acid → 2-Carbobenzyloxy-3,4,5-trimethoxybenzoic Acid

HRID 1384055

반응식

HRID 1384055 반응식
C([Li])(C)(C)C.Br[C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[C:13]([O:20][CH3:21])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].Cl>C1COCC1.O>[C:23]([C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[C:13]([O:20][CH3:21])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 3130972-Bromo-3,4,5-trimethoxybenzoic acidHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 211854922-Carbobenzyloxy-3,4,5-trimethoxybenzoic Acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

tert-Butyllithium (1.7M solution in pentane, 15 mmol) is added to a solution of 2-bromo-3,4,5-trimethoxybenzoic acid 5 (5 mmol, synthesis described in Example 12) in 50 mL of THF, while maintaining the temperature of the mixture below −95° C. After the addition is completed, the mixture is allowed to warm to −78° C. After 30 minutes, benzyl chloroformate (5 mmol) is added in one portion, and the mixture is allowed to warm to 0° C. Water (50 mL) is added, and then the pH of the mixture is carefully adjusted to 3 using 0.1 M HCl. The mixture is extracted with ethyl acetate (5×100 mL). The organic phases are dried over anhydrous Na2SO4 and concentrated in vacuo. The mixture is purified by flash chromatography to give the product as a colorless oil.

후처리

  1. temperaturewhile maintaining the temperature of the mixture below −95° C
  2. additionAfter the addition
  3. temperatureto warm to 0° C
  4. extractionThe mixture is extracted with ethyl acetate (5×100 mL)
  5. dry with materialThe organic phases are dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe mixture is purified by flash chromatography

출처 및 근거

ORD 기록
ord-814334da344e4ef58baecf6affa046b6
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06258360B1

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