Triphenylphosphine → 2-(4-[(E)-hex-2-enyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole

HRID 2121305Notes

Reaction equation

HRID 2121305 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])=[N:37][N: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])=[N:37][N: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 1358448412-(4-Hydroxyphenyl)-5-pentyl-1,3,4-thiadiazole

Product 1

HCID 234321202-(4-[(E)-hex-2-enyloxy]phenyl)-5-pentyl-1,3,4-thiadiazoleYield 20.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.95 g) is added in small portions to a solution of (E)-hex-2-en-1-ol (0.40 g), 2-(4-hydroxyphenyl)-5-pentyl-1,3,4-thiadiazole (0.71 g), diethylazodicarboxylate (0.63 g) in dry tetrahydrofuran (40 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 0.19 g of 2-(4-[(E)-hex-2-enyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole.

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-75a701761c7a44e982172c30ff28d4ad
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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