Sodium Hydroxide → N-(tert-butyl)-N-phenylformamide

HRID 41656

반응식

HRID 41656 반응식
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH:12](OC(=O)C)=[O:13].[OH-].[Na+]>C1COCC1>[C:1]([N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:12]=[O:13])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 75269Acetic-formic anhydrideHCID 254260N-(1,1-Dimethylethyl)benzenamine

생성물 1

HCID 3720775N-(tert-butyl)-N-phenylformamide수율 74.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1a (1.2212 g, 8.18 mmol) and acetic formic anhydride (1.2 mL, 15 mmol) in THF (10 mL) was stirred for 7 h at room temperature. To the reaction solution was added an aqueous NaOH solution (1.0 M, 20 mL) The organic phase was extracted with Et2O (30 mL×2) and was chromatographed (4:1 hexanes/EtOAc) to give 2a (1:1 mixture of isomers, 1.076 g, 74.2%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.72 (s, 0.5H), 8.16 (s, 0.5H), 7.51-7.29 (m, 3H), 7.19-6.99 (m, 2H), 1.40 (s, 9H); 13C NMR (75 MHz, CDCl3): δ 163.4, 162.6, 141.0, 138.2, 130.3, 130.1, 129.3, 129.2, 128.4, 57.7, 56.7, 31.0, 29.2. HRMS-ESI (m/z): [M+H]+ calcd for C11H15NO, 178.1226. found: 178.1228.

후처리

  1. extractionwas extracted with Et2O (30 mL×2)
  2. customwas chromatographed (4:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-884c8fe23cc942bd8aa8bd7c1f0f61a7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530687B2

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