Acrolein → HCID 18921999, 화합물

HRID 1289808노트

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HRID 1289808 반응식
[CH:1]1([C:5]([OH:15])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([OH:8])=[O:7])[CH2:4][CH2:3][CH2:2]1.[CH2:16]1[CH2:26][CH2:25][N:24]2[C:19](=N[CH2:21][CH2:22][CH2:23]2)[CH2:18][CH2:17]1.C(C=C)=O.[I-].[CH:32]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:36]C[CH2:34][CH2:33]1.C([Li])CCC>O1CCCC1.O.CCCCCC>[C:17]1(=[CH:16][CH2:26][CH2:25][N:24]2[CH2:23][CH2:22][CH:21]([O:7][C:6](=[O:8])[C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)([OH:15])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:18][CH2:19]2)[CH2:34][CH2:33][CH2:32][CH2:36]1

참가 물질

9

반응물 5

HCID 7847AcroleinHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 108890462-cyclobutyl-2-hydroxy-2-phenylacetic acidHCID 19082503Cyclopentyltriphenylphosphonium iodideHCID 178418339Butyllithium

생성물 1

HCID 18921999HCID 18921999, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

According to the method of A. Chesnyl et al. [Synthetic Communications, Vol. 20, pp. 3167-3180 (1990)], 50 mg of the 2-cyclobutyl-2-hydroxy-2-phenylacetic acid obtained in Step 1 of Example 1 and a catalytic amount of DBU were dissolved in 2 ml of tetrahydrofuran, and 15 μl of acrolein was added thereto at -15° C., followed by stirring for 20 minutes. The resulting solution was added at 0° C. to an ylide compound prepared from 156 mg of cyclopentyltriphenylphosphonium iodide and 200 μl of n-butyl lithium (as a 1.69M hexane solution), and this mixture was stirred at 0° C. for 30 minutes and then at room temperature for 4 hours. After the addition of 20 ml of water, the reaction mixture was extracted with ethyl acetate (30 ml×3). The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck); developing solvent: hexane/ethyl acetate=1/2] to obtain 2.0 mg of the title compound.

후처리

  1. customat -15° C.
  2. additionThe resulting solution was added at 0° C. to an ylide compound
  3. stirringwas stirred at 0° C. for 30 minutes
  4. waitat room temperature for 4 hours
  5. extractionthe reaction mixture was extracted with ethyl acetate (30 ml×3)
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. customthe resulting residue was purified by thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck); developing solvent: hexane/ethyl acetate=1/2]

출처 및 근거

ORD 기록
ord-f13720c0ff0242cfbadb6b1fd7208e9d
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750540

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