Diphenylacetonitrile → HCID 10681154, compound

HRID 1461138Notes

Reaction equation

HRID 1461138 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:18]1[CH2:22]OC[CH2:19]1>>[C:10]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:22][CH:18]=[CH2:19])[C:8]#[N:9])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 6837DiphenylacetonitrileHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Product 1

HCID 10681154HCID 10681154, compound

Procedure

A solution of 2,2-diphenylacetonitrile (9.15 g) in THF (22.5 ml) was added dropwise to a stirred slurry of 80% sodium hydride (2.85 g, washed twice with hexane) and THF, under nitrogen. The mixture was stirred vigorously until the evolution of gas ceased. Allyl bromide (6.3 g) was added by syringe, and the resultant mixture was stirred at room temperature for 18 hours. The mixture was carefully poured into ice water, and the aqueous mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water and brine (once each), dried (MgSO4), and rotary evaporated to yield 11.1 g of 2,2-diphenyl-4-pentenenitrile, as an oily product.

Workup

  1. washwashed twice with hexane) and THF
  2. additionAllyl bromide (6.3 g) was added by syringe
  3. stirringthe resultant mixture was stirred at room temperature for 18 hours
  4. additionThe mixture was carefully poured into ice water
  5. extractionthe aqueous mixture was extracted with ethyl acetate (3×)
  6. washThe combined extracts were washed with water and brine (once each),
  7. dry with materialdried (MgSO4)
  8. customrotary evaporated

Sources & evidence

ORD record
ord-6ced4fa403c249d0bb599d095ac63b41
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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