Dichloromethane → HCID 68008574, compound

HRID 535156Notes

Reaction equation

HRID 535156 reaction equation
[C:1]([C:8]1[CH:20]=[C:19]2[C:11]([C:12]3[CH:13]=[CH:14][C:15]([C:21](=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][C:17]=3[CH2:18]2)=[CH:10][CH:9]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(Cl)Cl.[C:31](#[N:34])[CH:32]=[CH2:33]>CO>[C:31]([CH2:32][CH2:33][C:18]1([CH2:33][CH2:32][C:31]#[N:34])[C:17]2[CH:16]=[C:15]([C:21](=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:14]=[CH:13][C:12]=2[C:11]2[C:19]1=[CH:20][C:8]([C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:9][CH:10]=2)#[N:34]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7855AcrylonitrileHCID 127211471,1'-(9H-Fluorene-2,7-diyl)di(hexan-1-one)

Product 1

HCID 68008574HCID 68008574, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3-neck 250-mL round bottom flask was equipped with a condenser, a nitrogen inlet, an addition funnel, and a magnetic stir bar. The flask was then charged with 14.50 g of 1-(7-hexanoyl-9H-fluoren-2-yl)-hexan-1-one and 80 mL of methylene chloride. TRITON B (0.80 g, 40% methanol solution) was then added, followed by the drop wise addition of acrylonitrile (4.67 g) at a rate that kept the reaction temperature below 35° C. The reaction was then stirred at ambient temperature for three hours. The solvent was then removed under reduced pressure and the resulting solid was crystallized from ethanol to give 12.60 g of the title compound. 1H NMR (CDCl3, 300 MHz) δ 8.11-8.03 (m, 4H), 7.89 (m, 2H), 3.04 (m, 4H), 2.55 (m, 4H), 1.81 (m, 4H), 1.56 (m, 4H), 1.44-1.38 (m, 8H), 0.94 (m, 6H).

Workup

  1. customA 3-neck 250-mL round bottom flask was equipped with a condenser, a nitrogen inlet, an addition funnel, and a magnetic stir bar
  2. customthe reaction temperature below 35° C
  3. customThe solvent was then removed under reduced pressure
  4. customthe resulting solid was crystallized from ethanol

Sources & evidence

ORD record
ord-574cc6d2c0fc4aa2a8ccef6085167e13
Source dataset
uspto-grants-2014_10
Patent number
US08854730B2

Reaction notes

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