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

HRID 543339ノート

反応式

HRID 543339 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-d9b61874131343f995d550eec3fd420a
出典データセット
uspto-grants-1987_04
特許番号
US04661617

反応ノート

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