4-Bromobutyric acid → 4-Bromobutanoic Acid 9-Fluorenylmethyl Ester

HRID 329544

반응식

HRID 329544 반응식
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH:8]1[C:20]2[CH:19]([CH2:21]O)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:8]1[C:20]2[CH:19]([CH2:21][O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][Br:1])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 2

HCID 758094-Bromobutyric acidHCID 904669H-Fluorene-9-methanol

생성물 1

HCID 145062184-Bromobutanoic Acid 9-Fluorenylmethyl Ester수율 86.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

DDC (6.00 g, 29 mmol) was added in one portion to a cooled solution (0° C.) of 4-bromobutyric acid (5.00 g, 29.9 mmol), 4-(dimethylamino)pyridine (353 mg, 2.9 mmol) and 9-fluorenemethanol (5.63 g, 25 mmol) in CH2Cl2 (150 mL). The mixture was allowed to stand at 4° C. for 18 h, and then filtered. The filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in EtOAc and the solution washed sequentially with 1N NaHCO3, 1N HCl and H2O. The solution was dried (Na2 -SO4) and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography on silica gel (200 g) using hexane-EtOAc (15:1) as the eluant to give the pure title compound as an oil (7.5 g).

후처리

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washthe solution washed sequentially with 1N NaHCO3, 1N HCl and H2O
  5. customThe solution was dried (Na2 -SO4)
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (200 g)

출처 및 근거

ORD 기록
ord-e881caaf12d945be80405e4641a3e0c4
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04891358

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