CID 406 → HCID 21321733, 화합물

HRID 261927노트

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HRID 261927 반응식
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].P(=O)([O-])[O-].C([Li])CCC.[CH2:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH:18]1[CH2:26][C:27](OC)=[O:28]>O1CCCC1.CCCCCC.C(O)(=O)C>[O:28]=[C:27]([CH2:26][CH:18]1[CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17]1)[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

참가 물질

8

반응물 4

HCID 406CID 406HCID 12958Dimethyl methylphosphonateHCID 14090225Methyl (2,3-dihydro-1H-inden-2-yl)acetateHCID 178418339Butyllithium

생성물 1

HCID 21321733HCID 21321733, 화합물

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A solution of 49.6 g (0.40 mole) dimethyl methylphosphonate (Aldrich) in 500 ml dry tetrahydrofuran is cooled to -78° in a dry nitrogen atmosphere. To the stirred phosphonate solution is added 188 ml of 2.34 M n-butyllithium in hexane solution (Alfa Inorganics, Inc.) dropwise over a period of 40 minutes at such a rate that the reaction temperature never rises above -65°. After an additional 5 minutes stirring at -78°, 36.0 g (0.20 mole) methyl (2-indanyl)acetate added dropwise at a rate that keeps the reaction temperature less than -70° (20 minutes). After 1.0 hour at -78° the reaction mixture is allowed to warm to ambient temperature, neutralized with 25 ml acetic acid and rotary evaporated to a white gel. The gelatinous material is taken up in 75 ml water, the aqueous phase extracted with 100 ml portions of choroform (3x), the combined organic extracts are backwashed (50 cc H2O), dried (MgSO4), and concentrated (water aspirator) to a crude residue and distilled, dimethyl 2-oxo-3-(2-indanyl) propylphosphonate.

후처리

  1. customthe reaction temperature less than -70° (20 minutes)
  2. waitAfter 1.0 hour at -78° the reaction mixture is allowed
  3. customrotary evaporated to a white gel
  4. extractionthe aqueous phase extracted with 100 ml portions of choroform (3x)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated (water aspirator) to a crude residue
  7. distillationdistilled

출처 및 근거

ORD 기록
ord-037457ea78c44e71a95ee566e044832e
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152527

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