CID 406 → HCID 21321733、化合物

HRID 261927ノート

反応式

HRID 261927 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 21321733HCID 21321733、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-037457ea78c44e71a95ee566e044832e
出典データセット
uspto-grants-1979_05
特許番号
US04152527

反応ノート

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