Triphenylphosphine → HCID 54378274, compound

HRID 349244Notes

Reaction equation

HRID 349244 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C(OCC)C.ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 615235-Phenyl-1-pentanolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 1

HCID 54378274HCID 54378274, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-phenylpentanol (3.7 mL), methyl 3-(4-hydroxyphenyl)propanoate (3.6 g), triphenylphosphine (5.77 g) and dichloromethane (200 mL) was added 1,1′-(azodicarbonyl)dipiperidine (5.55 g). The reaction mixture was stirred at room temperature for 4 days. Diethyl ether was added to the reaction mixture, which was filtered and the filtrate was concentrated. Hexane-diethyl ether (1:1) (200 mL) was added to the residue, which was filtered and the filtrate was concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1→4:1) to give the title compound (6.16 g) having the following physical data.

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated
  3. additionHexane-diethyl ether (1:1) (200 mL) was added to the residue, which
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-9f81043086a8428d98dbd4e338e45ab6
Source dataset
uspto-grants-2007_02
Patent number
US07179817B2

Reaction notes

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