CID 406 → HCID 21321734, 화합물

HRID 261921노트

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HRID 261921 반응식
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].P(=O)([O-])[O-].C([Li])CCC.[C:17]12([CH2:27][C:28](OC)=[O:29])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>O1CCCC1.CCCCCC.C(O)(=O)C>[O:29]=[C:28]([CH2:27][C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2)[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

참가 물질

8

반응물 4

HCID 406CID 406HCID 12958Dimethyl methylphosphonateHCID 141339Tricyclo(3.3.1.13,7)decane-1-acetic acid, methyl esterHCID 178418339Butyllithium

생성물 1

HCID 21321734HCID 21321734, 화합물

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A solution of 49.6 g (0.400 moles) dimethyl methylphosphonate (Aldrich) in 500 ml dry tetrahydrofuran was cooled to -78° in a dry nitrogen atmosphere. To the stirred phosphonate solution was 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 rose above -65°. After an additional 5 minutes stirring at -78°, 41.7 g (0.200 mole) methyl (1-adamantyl)-acetate was added dropwise at a rate that kept the reaction temperature less than -70° (20 minutes). After 1.0 hour at -78°, the reaction mixture was allowed to warm to ambient temperature, neutralized with 25 ml acetic acid and rotary evaporated to a white gel. The gelatinous material was taken up in 50 ml water, the aqueous phase extracted with 100 ml portions of methylene chloride (4x), the combined orgaic extracts were backwashed with water (4 × 100 ml), dried (MgSO4), and concentrated (water aspirator) to a crude residue and distilled, b.p 209°-212° (<0.02 mm) to give dimethyl 2-oxo-3-(1-adamantyl)propylphosphonate (2a ).

후처리

  1. customthe reaction temperature less than -70° (20 minutes)
  2. waitAfter 1.0 hour at -78°
  3. customrotary evaporated to a white gel
  4. extractionthe aqueous phase extracted with 100 ml portions of methylene chloride (4x)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated (water aspirator) to a crude residue
  7. distillationdistilled, b.p 209°-212° (<0.02 mm)

출처 및 근거

ORD 기록
ord-704c97ff8fdf44a189a2bfd360863807
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152527

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