Water → Ethyl 2-(3-bromo-4-(cyclopropylmethoxy)-5-nitrophenyl)-4-methylpentanoate

HRID 1183583노트

반응식

HRID 1183583 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].C([O-])([O-])=O.[Cs+].[Cs+].[CH:28]1([CH2:31]Br)[CH2:30][CH2:29]1.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[O:8][CH2:31][CH:28]1[CH2:30][CH2:29]1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 57995502Ethyl 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoate

생성물 1

HCID 57995564Ethyl 2-(3-bromo-4-(cyclopropylmethoxy)-5-nitrophenyl)-4-methylpentanoate수율 64.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of ethyl 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoate (4.1 g, 11.26 mmol) was taken in 50 ml of DMSO and to it added Cs2CO3 (3.02 g, 12.39 mmol). The reaction mixture was stirred at room temperature for 15 minutes and then added cyclopropylmethyl bromide (1.67 g, 12.39 mmol) dropwise. After completion of addition, the reaction mixture was stirred at 70° C. for 4 h. After completion of the reaction, it was poured into water (200 ml) and extracted with ethyl acetate (100 ml×3). The ethyl acetate layer was washed with 1N HCl, water and finally brine solution. The organic layer was then distilled off and the crude residue was purified by column chromatography using Ethyl acetate:hexane (1:3) as eluent provided 3 g of ethyl 2-(3-bromo-4-(cyclopropylmethoxy)-5-nitrophenyl)-4-methylpentanoate. 1H NMR (CDCl3): δ 8.20 (s 1H), 7.20 (s, 1H), 4.15 (q, 2H), 3.60 (t, 1H), 3.45 (d, 2H), 1.95-2.00 (m, 1H), 1.75-1.80 (m, 1H), 1.45-1.50 (m, 1H), 1.20 (t, 3H), 1.00 (m, 6H), 0.35-0.25 (m, 5H). Mass: (414, M+1,100%).

후처리

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred at 70° C. for 4 h
  3. customAfter completion of the reaction, it
  4. extractionextracted with ethyl acetate (100 ml×3)
  5. washThe ethyl acetate layer was washed with 1N HCl, water and finally brine solution
  6. distillationThe organic layer was then distilled off
  7. customthe crude residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-26a9e20519f24b4eb4381f712c110e65
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664249B2

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