Triphenylphosphine → 2-[(E)-hex-2-enyloxy]-5-(4'-hexylbiphenyl-4-yl)thiophene

HRID 2121309Notes

Reaction equation

HRID 2121309 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([OH:26])/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH3:25].O[C:28]1[S:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:41][CH:40]=3)=[CH:35][CH:34]=2)=[CH:31][CH:32]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:20]([O:26][C:28]1[S:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:40]=[CH:41][C:42]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:43][CH:44]=3)=[CH:35][CH:34]=2)=[CH:31][CH:32]=1)/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 53180422-Hexen-1-olHCID 5462977Diethyl azodicarboxylateHCID 234321732-Hydroxy-5-(4'-hexylbiphenyl-4-yl)thiophene

Product 1

HCID 234321812-[(E)-hex-2-enyloxy]-5-(4'-hexylbiphenyl-4-yl)thiopheneYield 19.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (1.4 g) is added in small portions to a solution of (E)-hex-2-en-1-ol (0.60 g), 2-hydroxy-5-(4′-hexylbiphenyl-4-yl)thiophene (0.50 g), diethylazodicarboxylate (0.80 g) in dry tetrahydrofuran (100 cm3) at 0° C. under an atmosphere of nitrogen. The reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the crude product was purified by column chromatography on silica gel using a 4:1 petroleum (40-60° C.) ether/ethyl acetate mixture as eluent, followed by recrystallisation from ethanol to yield 0.12 g of 2-[(E)-hex-2-enyloxy]-5-(4′-hexylbiphenyl-4-yl)thiophene.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe crude product was purified by column chromatography on silica gel using a 4:1 petroleum (40-60° C.) ether/ethyl acetate mixture as eluent
  3. customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-31d202eed6e74b5e96675609941c9056
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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