Triphenylphosphine → Methyl 2-(benzamido)-4-(3-phenylpropoxy)benzoate

HRID 1673402Notes

Reaction equation

HRID 1673402 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(C)C=CC=CC=1.[C:22]([NH:30][C:31]1[CH:40]=[C:39]([OH:41])[CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:42]1([CH2:48][CH2:49][CH2:50]O)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:22]([NH:30][C:31]1[CH:40]=[C:39]([O:41][CH2:50][CH2:49][CH2:48][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 31234BenzenepropanolHCID 57879368Methyl 2-(benzamido)-4-hydroxybenzoateHCID 66880968DIAD toluene

Product 1

HCID 57879320Methyl 2-(benzamido)-4-(3-phenylpropoxy)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.28 mL of 40% diisopropyl azodicarboxylate /toluene was added dropwise to 1 mL of tetrahydrofuran solution containing 0.10 g of methyl 2-(benzamido)-4-hydroxybenzoate, 0.060 mL of 3-phenyl-1-propanol and 0.15 g of triphenylphosphine at room temperature, and stirred at the same temperature for 2 hours and 30 minutes. The solvent was evaporated under reduced pressure, and the obtained residue was purified wish silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to obtain 45 mg of methyl 2-(benzamido)-4-(3-phenylpropoxy)benzoate as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified

Sources & evidence

ORD record
ord-68b9d42b514e402aa5651271af4b2f28
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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