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

HRID 1748999노트

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HRID 1748999 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-96286daf5a7e44eca3bb9f899c2f9178
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09155690B2

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