Water → ethyl (Z)-3-methyl-4-[4-(1-methylpropoxy)phenoxyl]-2-butenoate

HRID 543339

반응식

HRID 543339 반응식
[CH3:1][CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([CH3:28])=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C)C=O>[CH3:20]/[C:21](/[CH2:28][O:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH:2]([CH3:1])[CH2:3][CH3:4])=[CH:11][CH:10]=1)=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 138820044-(1-Methyl-1-propyloxy)-phenolHCID 53411540Ethyl-4-bromo-3-methyl-but-2-enoate (E/Z; 55/45)

생성물 1

HCID 13882007ethyl (Z)-3-methyl-4-[4-(1-methylpropoxy)phenoxyl]-2-butenoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 4-(1-methylpropoxy)phenol (0.84 g, 5.06 mmol) and potassium carbonate (0.66 g, 0.48 mmol) in 10 ml of dimethylformamide (DMF) at 5° is added ethyl 4-bromo-3-methyl-2-butenoate (1.0 g, 0.48 mmol). The mixture is allowed to warm to RT and is stirred at RT for 20 hours. The reaction mixture is poured into water and extracted with ether. The organic layer is washed with 10% sodium hydroxide to remove any starting phenol, dried and the solvent removed. The product is purified by preparative thin layer chromatography (prep. TLC). The second main band is collected to give ethyl (Z)-3-methyl-4-[4-(1-methylpropoxy)phenoxyl]-2-butenoate, MS m/e 292 (M+).

후처리

  1. extractionextracted with ether
  2. washThe organic layer is washed with 10% sodium hydroxide
  3. customto remove any starting phenol
  4. customdried
  5. customthe solvent removed
  6. customThe product is purified by preparative thin layer chromatography (prep. TLC)
  7. customThe second main band is collected

출처 및 근거

ORD 기록
ord-d9b61874131343f995d550eec3fd420a
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04661617

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