Benzyl Alcohol → (2RS,3SR)-2-benzyloxycarbonyl-5-oxotetrahydrofuran-3-carboxylic acid

HRID 581043

반응식

HRID 581043 반응식
[O:1]=[C:2]1[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH:4]([C:10]([OH:12])=[O:11])[CH2:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:28](O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(C)=O>[CH2:28]([O:8][C:7]([CH:5]1[CH:4]([C:10]([OH:12])=[O:11])[CH2:3][C:2](=[O:1])[O:6]1)=[O:9])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 98259Tetrahydro-5-oxofuran-2,3-dicarboxylic acid

생성물 1

HCID 18705291(2RS,3SR)-2-benzyloxycarbonyl-5-oxotetrahydrofuran-3-carboxylic acid

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

5.3 g of (2RS,3SR)-5-oxotetrahydrofuran-2,3-dicarboxylic acid was dissolved in 90 ml of acetone, and 6.6 g of N,N'-dicyclohexylcarbodiimide was added thereto, followed by stirring at room temperature for 2.5 hours. 3.3 ml of benzyl alcohol was added to the reaction solution, followed by stirring at the same temperature for 2 days. Insoluble matters were filtered off, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1+chloroform/methanol=50/1) to obtain 6.55 g of the above-identified compound as a yellow solid.

후처리

  1. stirringby stirring at the same temperature for 2 days
  2. filtrationInsoluble matters were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1+chloroform/methanol=50/1)

출처 및 근거

ORD 기록
ord-ec1dfca3ad4d4dd08be4353809871e80
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919786

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