Dimethyl Carbonate → 1-Oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester

HRID 2070581

反応式

HRID 2070581 の反応式
[H-].[Na+].CC(C)([O-])C.[K+].[C:9](=[O:14])([O:12][CH3:13])OC.[C:15]1(=[O:26])[C:20]2([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:19][CH2:18][CH2:17][CH2:16]1>O1CCCC1.[Cl-].[Na+].O.C(O)(=O)C>[CH3:13][O:12][C:9]([CH:16]1[CH2:17][CH2:18][CH2:19][C:20]2([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[C:15]1=[O:26])=[O:14]

参加物

8

反応物 4

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 573924Spiro(5.5)undecan-1-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 157014041-Oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

To a suspension of 60% sodium hydride (5.7 g) and potassium tert-butoxide (1.6 g) in tetrahydrofuran (200 mL) was added dimethyl carbonate (9.6 mL) at room temperature while stirring. The reaction mixture was heated under reflux. To the reaction mixture was added dropwise a solution of spiro[5.5]undecan-1-one (11.85 g) obtained in Step 1 in tetrahydrofuran (40 mL) over 1 hour, followed by heating the reaction mixture under reflux for 2 hours. After ice-cooling, acetic acid (14.6 mL) was added dropwise to the reaction mixture. Then, the reaction mixture was poured into saturated brine, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15) to give 1-oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester (13.02 g).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux
  3. temperatureby heating the reaction mixture
  4. temperatureunder reflux for 2 hours
  5. temperatureAfter ice-cooling
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15)

出典と根拠

ORDレコード
ord-65f5429401d14c5d9d02ae3beff46eda
出典データセット
uspto-grants-2012_10
特許番号
US08299296B2

関連ノート

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