Triphenylphosphine → HCID 23432059, compound

HRID 2121298Notes

Reaction equation

HRID 2121298 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[CH:33]=[CH:32][C:31]([C:34]2[S:35][C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:37][CH:38]=2)=[CH:30][CH:29]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:20]([O:26][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[S:35][C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:37][CH:38]=2)=[CH:32][CH:33]=1)/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 53180422-Hexen-1-olHCID 5462977Diethyl azodicarboxylateHCID 234323142-(4-Hydroxyphenyl)-5-pentylthiophene

Product 1

HCID 23432059HCID 23432059, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.53 g) was added in small portions to a solution of (E)-hex-2-en-1-ol (0.20 g), 2-(4-hydroxyphenyl)-5-pentylthiophene (0.50 g), diethylazodicarboxylate (0.35 g) in dry tetrahydrofuran (15 cm3) at 0° C. under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature overnight. The solvent was 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 0.10 g of 2-(4-[(E)-hex-2-enyloxy]phenyl)-5-pentylthiophene, K, 82° C., I.

Workup

  1. customThe solvent was 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-b47bd7ec54a84912addb895eb428161a
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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