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Tetrahydrofuran → Dimethyl 2-Oxo-3-methylheptylphosphonate

HRID 1076050
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HRID 1076050 반응식
C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].O1CCCC1.[CH3:18][CH:19]([CH2:25][CH2:26][CH2:27][CH3:28])[C:20](OCC)=[O:21]>C(O)(=O)C>[O:21]=[C:20]([CH:19]([CH3:18])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]
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참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 12958Dimethyl methylphosphonateHCID 12714009Ethyl 2-methylhexanoateHCID 178418339Butyllithium

생성물 1

HCID 12906670Dimethyl 2-Oxo-3-methylheptylphosphonate

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

n-Butyllithium (150 ml.) is slowly added to a solution of dimethyl methylphosphonate (25.6 g.) in 475 ml. of tetrahydrofuran (THF) at about -65° C. To the mixture is added a solution of racemic ethyl 2-methylhexanoate (18.4 g.) in 50 ml. of THF, and the resulting mixture is stirred at -70° C. for 2 hrs. Then, 16 ml. of acetic acid is added, and the mixture is concentrated under reduced pressure. The residue is mixed with dichloromethane (about 400 ml.) and water (about 50 ml.), shaken, and separated. The organic phase is dried over magnesium sulfate and concentrated. Distillation yields the title compound, 16.7 g., b.p. 126°-129° C./1 mm.

후처리

  1. customat about -65° C
  2. concentrationthe mixture is concentrated under reduced pressure
  3. additionThe residue is mixed with dichloromethane (about 400 ml.) and water (about 50 ml.)
  4. customseparated
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated
  7. distillationDistillation

출처 및 근거

ORD 기록
ord-56a0d23553c74198b7e957ef145ca66f
출처 데이터셋
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03954833

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