Tetrahydrofuran → HCID 15238027, compound

HRID 274755Notes

Reaction equation

HRID 274755 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[C:5]1([CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1>>[C:14]1([CH:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:12](=[O:13])[C:12]#[C:11][CH2:14][CH:2]2[CH2:1][CH2:21][C:20]3[C:10](=[CH:5][CH:6]=[CH:7][C:24]=3[O:23][CH3:22])[CH2:9]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 13696DiphenylacetaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 15238027HCID 15238027, compound

Procedure

To a mixture of ethylmagnesium bromide (5.7 ml; 3.0M/L in ether solution) and THF (40 ml) was added dropwise a solution of the compound prepared in reference example 30 (3.0 g) in THF (20 ml) over a 10 min period. The mixture was stirred for 2 h at room temperature. To the mixture was added a solution of diphenylacetaldehyde (2.94 g) in THF (10 ml). The mixture was stirred for 2 h. After quenched by addition of ammonium chloride, the mixture was extracted with ether. The extract was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate, and evaporated. To a solution of the residue in ether (50 ml) was added manganese (IV) oxide (2.7 g) at room temperature. The mixture was stirred for 2 h. The mixture was filtrated, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1) to give the title compound (2.41 g) having the following physical data.

Workup

  1. additionwas added dropwise a solution of the compound
  2. stirringThe mixture was stirred for 2 h
  3. customAfter quenched by addition of ammonium chloride
  4. extractionthe mixture was extracted with ether
  5. washThe extract was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  7. customevaporated
  8. additionTo a solution of the residue in ether (50 ml) was added manganese (IV) oxide (2.7 g) at room temperature
  9. stirringThe mixture was stirred for 2 h
  10. filtrationThe mixture was filtrated
  11. customevaporated
  12. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-b2ee9a4f1bda48a8bffa9885822e43ef
Source dataset
uspto-grants-1995_02
Patent number
US05389666

Reaction notes

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