Triphenylphosphine → HCID 131717527, compound

HRID 1885993Notes

Reaction equation

HRID 1885993 reaction equation
O[C@H:2]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:10]=2)[O:5][C:3]1=[O:4].[CH2:21]([O:29][C:30]1[CH:38]=[CH:37][C:33](C(O)=O)=[CH:32][CH:31]=1)[CH2:22][CH2:23][CH2:24][CH2:25]CCC.N([C:46]([O:48]CC)=[O:47])=NC(OCC)=O.[C:51]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:56]=CC=C[CH:52]=1>C1C=CC=CC=1>[CH3:52][CH2:51][CH2:56][CH:21]([O:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:37][C:38]=1[C@@:2]1([C:46]([OH:48])=[O:47])[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:10]=2)[O:5][C:3]1=[O:4])[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 172314-(Octyloxy)benzoic acidHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22845927HCID 22845927, compound

Product 1

HCID 131717527HCID 131717527, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 2 ml of benzene was dissolved 0.1 g of (2S,5R)-2-hydroxy-5-(4-pentyloxyphenyl)-δ-valerolactone, and 0.1 g of 4-octyloxybenzoic acid and 0.05 g of diethyl azodicarboxylate were added to the solution. Then 0.1 g of triphenylphosphine was added to the mixture and reaction was carried out by continuing stirring at room temperature overnight. The solvent was removed from the mixture by distillation and the obtained crude product was purified by the silica gel column chromatography to obtain 0.08 g of oily (2R,5S)-2-(4-octyloxy)- phenylcarboxy-5-(4-pentyloxyphenyl)-δ-valerolactone having the following properties.

Workup

  1. additionwere added to the solution
  2. customThe solvent was removed from the mixture by distillation
  3. customthe obtained crude product
  4. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-bdee4e11d5ce47288cf0e45276322474
Source dataset
uspto-grants-1992_09
Patent number
US05149462

Reaction notes

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