Ethyl Acetate → 914452-60-1

HRID 1009980노트

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HRID 1009980 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].CCOC(C)=O>C1COCC1.O.[Cl-].[Na+].O>[CH2:16]([O:15][C:13](=[O:14])[NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 775714-Bromobenzylamine

생성물 1

HCID 25018359914452-60-1수율 107.6%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

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온도
0 °C

실험 절차

A solution of 4-bromobenzylamine (5 g, 26.9 mmol) in THF (50 ml) and water (50 ml) was cooled down to 0° C. with sodium hydroxide (1.13 g, 28.2 mmol). Benzyl chloroformate (4.0 ml, 28.2 mmol) was added slowly and the reaction mixture was stirred at 0° C. for 1 h and at r.t. for 18 hours. Brine (50 ml) and EtOAc (50 mL) were added and the phases were separated. The aqueous phase was extracted with EtOAc (40 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness to yield a light pink solid (9.27 g, 100%). 1H NMR (300 MHz, CDCl3), δ: 4.34 (2 H, d, J=6.0 Hz, CH2NH), 5.14 (2 H, s, OCH2), 7.17 (2 H, d, J=8.1 Hz, Ar), 7.33-7.40 (5 H, m, Ar), 7.46 (2 H, d, J=8.3 Hz, Ar)

후처리

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with EtOAc (40 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-12873b7f7b9a41208151a2626fc12592
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973181B2

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