Triphenylphosphine → Pentyl benzoate

HRID 352268Notes

Reaction equation

HRID 352268 reaction equation
OCCCCCCOC1C=CC(C#CC2C=C3C(=CC=2)C=C(OCCCCCCOC(=O)C=C)C=C3)=CC=1.[CH2:39]([O:44][C:45](=[O:74])[C:46]1[CH:51]=[C:50](OC(=O)C2C=CC(OCCCCCCOC(=O)C=C)=CC=2)[CH:49]=[CH:48][C:47]=1O)[CH2:40][CH2:41][CH2:42][CH3:43].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:39]([O:44][C:45](=[O:74])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:40][CH2:41][CH2:42][CH3:43]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15452352HCID 15452352, compoundHCID 20730944HCID 20730944, compound

Product 1

HCID 16296Pentyl benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of acrylic acid 6-{6-[4-(6-hydroxyhexyloxy)phenylethynyl]-naphthalen-2-yloxy)hexyl ester (1.05 g), 5-[4-(6-acryloyloxyhexyloxy)benzoyloxy]-2-hydroxybenzoic acid pentyl ester (1.12 g) and triphenylphosphine (0.59 g) in tetrahydrofuran (20 ml) was added under argon and in a dropwise fashion diethyl azodicarboxylate (DEAD, 0.39 g). Upon complete addition, the reaction mixture was stirred at room temperature overnight, and the solvent was then removed under reduced pressure to give a residue which was purified by flash chromatography using a silica-gel column and cyclohexane/ethyl acetate (8/2) as eluent to give 0.66 g of 5-[4-(6-acryloyloxyhexyloxy)benzoyloxy]-2-[6-[4-[6-(6-acryloyloxyhexyloxy)naphtha len-2-ylethynyl]phenoxy]hexyloxy]benzoyloxy]benzoic acid pentyl ester as white crystalline material. K 39° C. N 113° C. I.

Workup

  1. additionUpon complete addition
  2. customthe solvent was then removed under reduced pressure
  3. customto give a residue which
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-c71d5f687f5849139cf10fff295dd295
Source dataset
uspto-grants-2004_06
Patent number
US06746729B1

Reaction notes

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