Triphenylphosphine → HCID 22988438, compound

HRID 987143Notes

Reaction equation

HRID 987143 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](O)=[CH:5][CH:4]=1)[CH3:2].[CH2:10]([O:12][CH:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:11].N(C(N1CCCCC1)=O)=NC(N1CCC[CH2:33][CH2:32]1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:10]([O:12][CH:13]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:2][CH2:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:32][CH3:33])=[CH:5][CH:4]=2)=[CH:24][CH:25]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:11]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 312424-EthylphenolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 22988438HCID 22988438, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Ethyl-phenyl alcohol (0.45 g, 3 mmol) and ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate (0.86 g, 3.6 mmol) were mixed in dichloromethane (15 ml). 1,1′-(Azodicarbonyl)dipiperidine (0.91 g, 3.6 mmol) and triphenylphosphine (0.95 g, 3.6 mmol) were then added respectively. The mixture was stirred at room temperature overnight and filtered. The filtrate was evaporated to dry in vacuum. Column chromatography of the residue on silica gel using ethyl acetate/heptane (gradient 10:90 to 50:50) as eluant gave 0.49 g desired product, yield 44%.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customto dry in vacuum

Sources & evidence

ORD record
ord-d666ebde036a4b7aaf45833792a892a9
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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