Acetylenedicarbonitrile → HCID 178444402, compound

HRID 246791Notes

Reaction equation

HRID 246791 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13]/[CH:14]=[CH:15]/[CH:16]=[CH:17][CH2:18][CH2:19][CH3:20])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:21]([C:23]#[C:24][C:25]#[N:26])#[N:22]>O1CCCC1.C1(C=CC(O)=CC=1)O>[C:21]([C:23]1[CH:17]([CH2:18][CH2:19][CH3:20])[CH:16]=[CH:15][CH:14]([CH2:13][CH2:12][C@H:9]2[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)[C:24]=1[C:25]#[N:26])#[N:22]

Participants

5

Reactant 2

HCID 14068AcetylenedicarbonitrileHCID 178443361HCID 178443361, compound

Product 1

HCID 178444402HCID 178444402, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

9.5 g of 1-(trans-4-pentylcyclohexyl)-3,5-trans-nonadiene were dissolved in 62 ml of tetrahydrofuran in a round flask and treated with 14 mg of hydroquinone. A solution of 3.2 g of dicyanoacetylene in 18 ml of tetrahydrofuran was subsequently added by means of a pipette and the pipette was rinsed twice with 9 ml of tetrahydrofuran each time. The mixture was stirred at room temperature for 2.5 hours and then overnight at 40°-45° C. (bath temperature) under nitrogen. The dark brown solution was thereafter concentrated in vacuo. The resulting dark brown oil (10.9 g) was chromatographed on silica gel using hexane, hexane/toluene (volume ratio 1:1) and toluene, there being obtained 4.2 g of unreacted 3-cis, 5-trans-diene as a colourless oil and 7.4 g of 1,2-dicyano-3-[2-(trans-4-pentylcyclohexyl)ethyl]-6-propyl-1,4-cyclohexadiene as a slightly yellowish oil.

Workup

  1. washthe pipette was rinsed twice with 9 ml of tetrahydrofuran each time
  2. customovernight
  3. customat 40°-45° C.
  4. concentrationThe dark brown solution was thereafter concentrated in vacuo
  5. customThe resulting dark brown oil (10.9 g) was chromatographed on silica gel

Sources & evidence

ORD record
ord-b70d2be71f21451a9f6ba821794ef50c
Source dataset
uspto-grants-1987_11
Patent number
US04704005

Reaction notes

Loading…