Triethylamine → E-4-(Carbo-tert.-butoxy)-4'-(4-carbo-tert.-butoxystyryl)tolan

HRID 974215Notes

Reaction equation

HRID 974215 reaction equation
CCN(CC)CC.Br[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1.[C:30]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][C:39]([C:42]#[CH:43])=[CH:38][CH:37]=1)([CH3:33])([CH3:32])[CH3:31]>C(#N)C.[Cu]I>[C:35]([C:36]1[CH:41]=[CH:40][C:39]([C:42]#[C:43][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)=[CH:38][CH:37]=1)([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:44]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13965008Tert-butyl 4-ethynylbenzoateHCID 573054164-Bromo-4'-carbo-tert.-butoxystilbene

Product 1

HCID 131717083E-4-(Carbo-tert.-butoxy)-4'-(4-carbo-tert.-butoxystyryl)tolan

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent2×

Procedure

300 ml of NEt3 and 20.46 g of Pφ3 are added under nitrogen to 234 g of 4-bromo-4'-carbo-tert.-butoxystilbene in 1 l of absolute acetonitrile. Nitrogen is passed through the stirred suspension for 20 minutes and 9.12 g of (Pφ3)2PdCl2 and 2.5 g of copper(I)iodide are then added. 144 g of 4-Ethinyl benzoic acid tert.-butyl ester dissolved in 1 l of absolute acetonitrile are then added dropwise under reflux over a period of 6 hours and the reaction mixture is boiled under reflux overnight. The hot product obtained after suction filtration is dissolved in CH2Cl2, washed several times with H2O and dried and the solvent is removed.

Workup

  1. additionare then added dropwise
  2. temperatureunder reflux over a period of 6 hours
  3. temperatureunder reflux overnight
  4. customThe hot product obtained
  5. filtrationafter suction filtration
  6. dissolutionis dissolved in CH2Cl2
  7. washwashed several times with H2O
  8. customdried
  9. customthe solvent is removed

Sources & evidence

ORD record
ord-55e7a4ee3d36431cac4a797bb1cca528
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

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