2-[2,4-Bis(benzyloxy)phenyl]acetic Acid → 2-(2,4-Bis(benzyloxy)phenyl)ethanol

HRID 1595483노트

반응식

HRID 1595483 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[CH2:23][C:24](O)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)C.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][OH:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 50283782-[2,4-Bis(benzyloxy)phenyl]acetic Acid

생성물 1

HCID 148029092-(2,4-Bis(benzyloxy)phenyl)ethanol수율 43.5%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

10 ml (20 mmole) 2 M borane dimethyl sulfide complex in diethyl ether was slowly added to 6.3 g (18.1 mmole) 2,4-dibenzyloxyphenyl acetic acid dissolved in 50 ml dry tetrahydrofuran cooled on an ice bath under nitrogen and then stirred for 7 days at room temperature. The reaction was quenched with water and extracted with ethyl acetate, dried with magnesium sulfate and evaporated. The crude product was purified by chromatography on silica gel using dichloromethane/methanol as eluent to give 2.63 g of the desired product and a mixture of 2,4-dibenzyloxyphenyl acetic acid and the desired product. The mixture was dissolved in 100 ml ethyl acetate, 0.152 g (4 mmole) lithium aluminum hydride was added in portions and the mixture was stirred at room temperature for 6 hours. After 4 hours some more lithium aluminum hydride was added. The reaction was quenched with 1% hydrochloric acid and the solution was filtered. The filtrate was dried with magnesium sulfate and evaporated in vacuo to give 1.3 g more of 2-[2,4-di(benzyloxy)phenyl]-1-ethanol (total yield 3.9 g, 64.4%).

후처리

  1. temperaturecooled on an ice bath under nitrogen
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customThe crude product was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-46d0892063484aa685346da4aa3f1d14
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288096B1

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