Ethanol → Ethyl 2-(4-formyl-2-methoxyphenoxy)-2-methylpropanoate

HRID 1748999ノート

反応式

HRID 1748999 の反応式
C(O)C.C(O[Na])C.[O:8]=[CH:9][C:10]1[CH:18]=[CH:17][C:15]([OH:16])=[C:12]([O:13][CH3:14])[CH:11]=1.Br[C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[CH:9]([C:10]1[CH:18]=[CH:17][C:15]([O:16][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:12]([O:13][CH3:14])[CH:11]=1)=[O:8]

参加物

6

反応物 4

HCID 702EthanolHCID 1183VanillinHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178474001HCID 178474001、化合物

生成物 1

HCID 71497692Ethyl 2-(4-formyl-2-methoxyphenoxy)-2-methylpropanoate収率 36%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

In a co-solvent including ethanol (3 mL) and DMF (3 mL), IN ethoxy sodium (NaOEt) (2.96 mL, 2.96 mmol) was added dropwise to a solution including vanillin (300 mg, 1.97 mmol) and ethyl α-bromoisobutyrate (0.43 mL, 2.93 mmol), and then, the reaction mixture was heated at a temperature of 80° C. overnight. Ethanol was evaporated, and the residual was distributed between ether and water, and an organic layer was dried, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (EtOAc) (4:1) to obtain Compound 122a (188.7 mg, 36%).

後処理

  1. customEthanol was evaporated
  2. customan organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-96286daf5a7e44eca3bb9f899c2f9178
出典データセット
uspto-grants-2015_10
特許番号
US09155690B2

反応ノート

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