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

HRID 233346노트

반응식

HRID 233346 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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 THF 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, 9.72 g (26%)

후처리

  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

출처 및 근거

ORD 기록
ord-880bf072625541a886a25efd497def86
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591887

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