Ammonium Chloride → 4,4-Diphenyl-5-hydroxyl-6-heptenenitrile

HRID 1781519Notes

Reaction equation

HRID 1781519 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH:12]=[O:13])[CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:20]([Mg]Br)=[CH2:21].O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH:12]([OH:13])[CH:20]=[CH2:21])[CH2:8][CH2:9][C:10]#[N:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 196102744,4-Diphenyl-4-formylbutanenitrileHCID 178420667HCID 178420667, compound

Product 1

HCID 190457414,4-Diphenyl-5-hydroxyl-6-heptenenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon gas, 4,4-diphenyl-4-formylbutanenitrile (5.0 g) was dissolved in dry tetrahydrofuran (200 ml). Then, 1M vinylmagnesium bromide-tetrahydrofuran (30 ml) was added dropwise -40° C. After completion of addition, the reaction temperature was allowed to rise gradually to 0° C. (over 3 hours). After completion of the reaction, a saturated aqueous solution of ammonium chloride was added to the reaction mixture and the insoluble matter was filtered off. The filtrate was extracted with ethyl acetate, washed, dried, and concentrated and the group was purified by silica gel column chromatography. The active fraction was concentrated to provide the title compound as oil (5.4 g).

Workup

  1. additionAfter completion of addition
  2. customto rise gradually to 0° C.
  3. custom(over 3 hours)
  4. customAfter completion of the reaction
  5. filtrationthe insoluble matter was filtered off
  6. extractionThe filtrate was extracted with ethyl acetate
  7. washwashed
  8. customdried
  9. concentrationconcentrated
  10. customthe group was purified by silica gel column chromatography
  11. concentrationThe active fraction was concentrated

Sources & evidence

ORD record
ord-206c74739b404c849cda9be7a167a4f0
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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