Triethylamine → 4-((6-Acryloyloxy)hexyloxy)-4'-cyanobiphenyl

HRID 742518Notes

Reaction equation

HRID 742518 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32]>O1CCCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 111739504'-(6-Hydroxyhexyloxy)-4-cyanobiphenyl

Product 1

HCID 114167954-((6-Acryloyloxy)hexyloxy)-4'-cyanobiphenylYield 70.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.26 g (4.27 mmol) of the resulting compound (9) and 1.8 ml (24.8 mmol) of anhydrous triethylamine dissolved in 20 ml of tetrahydrofuran under argon atmosphere was added dropwise 5 ml of an tetrahydrofuran solution containing 0.38 ml (4.08 mmol) of acryloyl chloride. The whole was stirred at room temperature overnight, thereby a salt precipitated. After addition of water to the reaction mixture, the whole was extracted with diethyl ether. The extract was purified by silica gel column chromatography. The resulting pale yellow solid was recrystallized from methanol to obtain 1.01 g of 4-cyano-4'-(6-acryloxyhexyloxy)biphenyl (10) (yield: 67.7%).

Workup

  1. customa salt precipitated
  2. additionAfter addition of water to the reaction mixture
  3. extractionthe whole was extracted with diethyl ether
  4. customThe extract was purified by silica gel column chromatography
  5. customThe resulting pale yellow solid was recrystallized from methanol

Sources & evidence

ORD record
ord-007c31271c7848f7a18e4e8afd2e4329
Source dataset
uspto-grants-1996_09
Patent number
US05554706

Reaction notes

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