Methyl Acrylate → Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

HRID 1898760ノート

反応式

HRID 1898760 の反応式
[C:1]([O:4][C:5]1[CH:12]=[C:11](Br)[C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>CN(C=O)C.CCOCC.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([CH:9]=[O:10])=[C:11]([CH:12]=1)[CH:25]=[CH:24][C:23]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2]

参加物

8

反応物 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 2623485-Bromo-4-formyl-2-methoxyphenyl acetate

生成物 1

HCID 53756943Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

試薬・触媒・溶媒 4

HCID 178419050HCID 178419050、化合物触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
135 °C

実験手順

To a degassed solution of 4-acetoxy-6-bromo-3-methoxybenzaldehyde (15.4 g), and bis(triphenylphosphine)palladium (11) (1.2 g) in DMF (150 ml) is added triethylamine (31.9 ml) and methyl acrylate (19.6 g). The mixture is heated 135° C. for about 1.5 hours, cooled to room temperature and diluted with ether and water. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 33% ethyl acetate in hexanes, then methylene chloride, to give the desired product.

後処理

  1. temperaturecooled to room temperature
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC
  7. washeluting with 33% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-6d60ba4013af443b98f7ff64911150e8
出典データセット
uspto-grants-1996_11
特許番号
US05571506

反応ノート

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