Sodium hydride → methyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

HRID 2353416ノート

反応式

HRID 2353416 の反応式
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[H-].[Na+]>C(=O)(OC)OC.C1(C)C=CC=CC=1>[O:10]=[C:7]1[CH2:6][CH2:5][C:4]2([O:3][CH2:2][CH2:1][O:11]2)[CH2:9][CH:8]1[C:4]([O:3][CH3:2])=[O:11]

参加物

5

反応物 2

HCID 24758Sodium hydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

生成物 1

HCID 4088708methyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 12021Dimethyl Carbonate溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 1,4-cyclohexanedione monoethylene ketal (1.00 g, 6.4 mmol) in dimethyl carbonate (6 mL) at room temperature was added sodium hydride (0.31 g, 7.7 mmol). The mixture was heated at 80° C. for 20 min and then diluted with dry toluene (20 mL). The mixture was stirred for an additional 3 h at 80° C., cooled to room temperature, quenched with water, and then extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and evaporated to yield the crude product which was purified by Biotage® chromatography (silica gel, ethyl acetate in hexanes gradient 30-42%) to yield the title compound.

後処理

  1. temperaturecooled to room temperature
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto yield the crude product which
  7. customwas purified by Biotage® chromatography (silica gel, ethyl acetate in hexanes gradient 30-42%)

出典と根拠

ORDレコード
ord-9ab3b5230e764964859ea2eb38939271
出典データセット
uspto-grants-2010_07
特許番号
US07750034B2

反応ノート

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