Triphenylphosphine → 1-(4-[(E)-hex-2-enyloxy]phenyl)-4-pentylbicyclo[2.2.2]octane

HRID 635133Notes

Reaction equation

HRID 635133 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].[CH2:27]([C:32]12[CH2:39][CH2:38][C:35]([C:40]3[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=3)([CH2:36][CH2:37]1)[CH2:34][CH2:33]2)[CH2:28][CH2:29][CH2:30][CH3:31].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:20]([O:26][C:43]1[CH:44]=[CH:45][C:40]([C:35]23[CH2:38][CH2:39][C:32]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:37][CH2:36]2)[CH2:33][CH2:34]3)=[CH:41][CH:42]=1)/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 53180422-Hexen-1-olHCID 5462977Diethyl azodicarboxylateHCID 21257800Phenol, 4-(4-pentylbicyclo[2.2.2]oct-1-yl)-

Product 1

HCID 212577911-(4-[(E)-hex-2-enyloxy]phenyl)-4-pentylbicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.34 g, 0.0013 mol) was added in small portions to a solution of (E)-hex-2-en-1-ol (0.13 g, 0.0013 mol), 4-(4-pentylbicyclo[2.2.2]octyl)phenol (0.35 g, 0.0013 mol), diethylazodicarboxylate (0.22 g, 0.0013 mol) in dry tetrahydrofuran (20 cm3), cooled in an ice bath 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 9:1 petroleum ether (40-60° C./ethyl acetate mixture as eluent, followed by recrystallisation from ethanol to yield 0.18 g (39%), K 69° C., SA-N 59° C., N-I 134° C.

Workup

  1. temperaturecooled in an ice bath under an atmosphere of nitrogen
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel using a 9:1 petroleum ether (40-60° C./ethyl acetate mixture as eluent
  4. customfollowed by recrystallisation from ethanol
  5. customto yield 0.18 g (39%), K 69° C., SA-N 59° C., N-I 134° C.

Sources & evidence

ORD record
ord-20aad75121be4c4ab75a9846bc46596a
Source dataset
uspto-grants-2001_02
Patent number
US06187393B1

Reaction notes

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