Benzyl Bromide → HCID 178501330, 화합물

HRID 409482노트

반응식

HRID 409482 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)=[O:4].[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@H:7]([O:9][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1)=[O:4]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12815112Cyclobutanecarboxylic acid, 3-hydroxy-, methyl ester

생성물 1

HCID 178501330HCID 178501330, 화합물수율 34.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a solution of cis-trans mixture of 3-hydroxy-cyclobutanecarboxylic acid methyl ester (1.30 g, 10 mmol) in DMF (13 mL) is added 50% NaH (720 mg, 15 mmol) at 0° C. After stirring at 0° C. for 15 min, benzyl bromide (1.43 ml, 12 mmol) is added at 0° C. The mixture is stirred at room temperature for 2 hours, and quenched with H2O. The solution is extracted with EtOAc. The organic layer is washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give trans-3-benzyloxy-cyclobutanecarboxylic acid methyl ester (750 mg, 34.1%); TLC (hexane/EtOAc, 5:1) Rf 0.35.

후처리

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. customquenched with H2O
  3. extractionThe solution is extracted with EtOAc
  4. washThe organic layer is washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bb0e54cd38844061b868a46be9bd3bdb
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759365B2

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