Acetic Acid → Dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate

HRID 964772ノート

反応式

HRID 964772 の反応式
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.[CH3:13][C:14]([CH3:24])([CH2:20][CH2:21][CH2:22][CH3:23])[C:15](OCC)=[O:16].C(O)(=O)C>C1COCC1>[CH3:13][C:14]([CH3:24])([CH2:20][CH2:21][CH2:22][CH3:23])[C:15](=[O:16])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 12958Dimethyl methylphosphonateHCID 3024116Ethyl dimethylhexanoateHCID 178418339Butyllithium

生成物 1

HCID 13018035Dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of dimethyl methylphosphonate (35.0 ml) in THF (300 ml) was cooled to -78° C., to which n-butyllithium (1.6 - M, 196 ml) was added dropwise. After stirring at -78° C. for one hour, a solution of ethyl 2,2-dimethylcaproate (27 g) in dry TEF was added. The reaction solution was stirred at -78° C. for one hour, and then at room temperature for additional 2 hours. The reaction solution was cooled to 0° C. and acetic acid (18 ml) was added thereto. The crude product obtained after the conventional work-up was distilled under reduced pressure and the resulting fraction (>130° C.) was chromatographed to give dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate. Yield, 9.72g (26%)

後処理

  1. additionwas added dropwise
  2. stirringThe reaction solution was stirred at -78° C. for one hour
  3. waitat room temperature for additional 2 hours
  4. temperatureThe reaction solution was cooled to 0° C.
  5. customThe crude product obtained after the conventional work-up
  6. distillationwas distilled under reduced pressure
  7. customthe resulting fraction (>130° C.) was chromatographed

出典と根拠

ORDレコード
ord-3a48bdfe9644443abf8ab3d5534bc6e8
出典データセット
uspto-grants-1998_06
特許番号
US05770759

反応ノート

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