Triphenylphosphine → (2R,5R)-(4'-octyloxy-3'-cyanobenzoyloxy)-5-hexyl-delta-valerolactone

HRID 893251Notes

Reaction equation

HRID 893251 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][C:25]=1[C:33]#[N:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].N(C(OCC)=O)=NC(OCC)=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:32]=[CH:31][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:26][C:25]=1[C:33]#[N:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14645393(2S,5R)-hydroxy-5-hexyl-delta-valerolactoneHCID 189964913-Cyano-4-(octyloxy)benzoic acid

Product 1

HCID 22844670(2R,5R)-(4'-octyloxy-3'-cyanobenzoyloxy)-5-hexyl-delta-valerolactoneYield 45.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 1 ml of dehydrated benzene were suspended 100 mg of (2S,5R)-2-hydroxy-5-hexyl-δ-valerolactone synthesized in the same manner as described in Referential Example 2 and 120 mg of 4-octyloxy-3-cyanobenzoic acid, and 0.1 ml of diethyl azodicarboxylate was added to the suspension with stirring at room temperature. Then, 150 mg of triphenylphosphine was added to the mixture and reaction was carried out overnight with stirring. The reaction mixture was concentrated under a reduced pressure and the residue was separated and purified by the silica gel column chromatography using an n-hexane/benzene (1/4) mixed solvent as the developing solvent. Recrystallization from ethanol gave 90 mg of (2R,5R)-(4'-octyloxy-3'-cyanobenzoyloxy)-5-hexyl-δ-valerolactone. When the phase transition behavior of the obtained compound was measured by a differential thermal scanning calorimeter and a polarization microscope, the following results were obtained: ##STR88##

Workup

  1. customsynthesized in the same manner
  2. additionwas added to the suspension
  3. stirringwith stirring
  4. concentrationThe reaction mixture was concentrated under a reduced pressure
  5. customthe residue was separated
  6. custompurified by the silica gel column chromatography
  7. additionmixed solvent as the developing solvent
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-acbc881978034fda877842dc45e78b36
Source dataset
uspto-grants-1992_06
Patent number
US05124069

Reaction notes

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