Triphenylphosphine → Ethyl (2R)-2-[4-(1-dodecyl-5-methyl-1H-pyrrol-2-yl)phenoxy]-3-phenylpropanoate

HRID 1072709Notes

Reaction equation

HRID 1072709 reaction equation
[CH2:1]([N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O[C@@H:27]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH2:1]([N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[C:19]1[CH:24]=[CH:23][C:22]([O:25][C@H:27]([CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9877619Ethyl phenyllactate, (-)-HCID 223877044-(1-dodecyl-5-methyl-1H-pyrrol-2-yl)phenol

Product 1

HCID 86588892Ethyl (2R)-2-[4-(1-dodecyl-5-methyl-1H-pyrrol-2-yl)phenoxy]-3-phenylpropanoateYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(1-dodecyl-5-methyl-1H-pyrrol-2-yl)phenol (2.97 g, 8.70 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.86 g, 9.58 mmol) and triphenylphosphine (2.51 g, 9.57 mmol) in toluene (120 ml) was added diethyl azodicarboxylate (1.67 g, 9.57 mmol) and the mixture was refluxed for 20 hours under heating. The insoluble matter was filtered out and the filtrate was diluted with ethyl acetate. The obtained solution was washed with water and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance. 1.49 g (yield: 33%)

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. temperatureunder heating
  3. filtrationThe insoluble matter was filtered out
  4. additionthe filtrate was diluted with ethyl acetate
  5. washThe obtained solution was washed with water
  6. dry with materialdried over magnesium sulfate anhydride
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
  9. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-f0d5fc47f90543568b514435fc4df75c
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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