Acrolein → HCID 18921999, compound

HRID 1289808Notes

Reaction equation

HRID 1289808 reaction equation
[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

Participants

9

Reactant 5

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

Product 1

HCID 18921999HCID 18921999, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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]

Sources & evidence

ORD record
ord-f13720c0ff0242cfbadb6b1fd7208e9d
Source dataset
uspto-grants-1998_05
Patent number
US05750540

Reaction notes

Loading…