Methanol → Ethyl 4-methoxy-3-oxobutanoate

HRID 579467

반응식

HRID 579467 반응식
[H-].[Na+].C[OH:4].Br[C:6]1[C:7](=O)[O:8][C:9]2C(C=1C)=C[CH:12]=[C:11]([OH:17])[CH:10]=2.CN([CH:22]=[O:23])C>Cl>[CH3:22][O:23][CH2:12][C:11](=[O:17])[CH2:10][C:9]([O:8][CH2:7][CH3:6])=[O:4]

참가 물질

6

반응물 4

HCID 887MethanolHCID 6228Dimethylformamide3회HCID 24758Sodium hydrideHCID 53375453-Bromo-7-hydroxy-4-methylchromen-2-one

생성물 1

HCID 12645099Ethyl 4-methoxy-3-oxobutanoate수율 15.1%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
0 °C

실험 절차

NaH (7.71 g, 192.7 mmol) was suspended in DMF (110 mL). The solution of MeOH (2.64 g, 82.5 mmol) in DMF (55 mL) was added drop wise at 0° C. After that, the mixture was stirred at 0° C. for 30 min. The solution of compound 1 (9.54 g, 57.9 mmol) in DMF (55 mL) was added dropwise at 0° C., then the reaction mixture was allowed to warm slowly to RT and stirred for 16 h. The reaction mixture was diluted with 1N HCl (400 mL), extracted with MTBE (250 mL×3). The combined organic layer was washed with H2O (200 mL×5), dried over Na2SO4, filtered, concentrated, purified by silica gel column (PE:EA=10:1) afforded ethyl 4-methoxy-3-oxobutanoate (1.4 g, 15.1%) as light yellow oil.

후처리

  1. temperatureto warm slowly to RT
  2. stirringstirred for 16 h
  3. extractionextracted with MTBE (250 mL×3)
  4. washThe combined organic layer was washed with H2O (200 mL×5)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column (PE:EA=10:1)

출처 및 근거

ORD 기록
ord-9e7544d2fee74e90bb23995b25649632
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040714B2

연결된 노트

불러오는 중…