Methanol → Ethyl 4-methoxy-3-oxobutanoate

HRID 579467

反応式

HRID 579467 の反応式
[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]

参加物

6

反応物 4

HCID 887MethanolHCID 6228Dimethylformamide3 回HCID 24758Sodium hydrideHCID 53375453-Bromo-7-hydroxy-4-methylchromen-2-one

生成物 1

HCID 12645099Ethyl 4-methoxy-3-oxobutanoate収率 15.1%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9e7544d2fee74e90bb23995b25649632
出典データセット
uspto-grants-2015_05
特許番号
US09040714B2

関連ノート

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