Triphenylphosphine → (2S,5R)-2-(4-octyloxybenzoyloxy)-5-hexyl-delta-valerolactone

HRID 893250Notes

Reaction equation

HRID 893250 reaction equation
[OH:1][C@H:2]1[CH2:8][CH2:7][C@@H:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[O:5][C:3]1=[O:4].[CH2:15]([O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].N(C(O)=O)=NC(O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH2:15]([O:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]([O:1][C@H:2]2[CH2:8][CH2:7][C@@H:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[O:5][C:3]2=[O:4])=[O:29])=[CH:31][CH:32]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 172314-(Octyloxy)benzoic acidHCID 415805Diazenedicarboxylic acidHCID 14645393(2S,5R)-hydroxy-5-hexyl-delta-valerolactone

Product 1

HCID 57087713(2S,5R)-2-(4-octyloxybenzoyloxy)-5-hexyl-delta-valerolactoneYield 41.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In dehydrated benzene were dispersed 200 mg of (2S,5R)-hydroxy-5-hexyl-δ-valerolactone synthesized in the same manner as described in Referential Example 4, 250 mg of p-octyloxybenzoic acid and 200 μl of azodicarboxylic acid, and 270 mg of triphenylphosphine was added to the dispersion and reaction was carried out with stirring overnight. The reacted solution was concentrated, and the concentrate was separated and purified by the silica gel column chromatography using n-hexane/benzene as the developing solvent. The obtained product was recrystallized from methanol to obtain 180 mg of (2S,5R)-2-(4-octyloxybenzoyloxy)-5-hexyl-δ-valerolactone. The NMR spectrum of the obtained compound is shown in FIG. 1. The results of the measurement of the phase transition behavior by a differential thermal scanning calorimeter and a polarization microscope are shown below: ##STR23##

Workup

  1. customsynthesized in the same manner
  2. additionwas added to the dispersion and reaction
  3. concentrationThe reacted solution was concentrated
  4. customthe concentrate was separated
  5. custompurified by the silica gel column chromatography
  6. customThe obtained product was recrystallized from methanol

Sources & evidence

ORD record
ord-d9eaab0bb47a4c8b87a223ec62945739
Source dataset
uspto-grants-1992_06
Patent number
US05124069

Reaction notes

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