Methyl Salicylate → Methyl 2-(2-(pyrrolidin-1-yl)ethoxy)benzoate

HRID 1012081Notes

Reaction equation

HRID 1012081 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:43][CH3:44])(=[O:42])[C:35]1[C:36](=[CH:38][CH:39]=[CH:40][CH:41]=1)[OH:37].O[CH2:46][CH2:47][N:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1>C1COCC1>[CH3:44][O:43][C:34](=[O:42])[C:35]1[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=1[O:37][CH2:46][CH2:47][N:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1

Participants

6

Reactant 4

HCID 4133Methyl SalicylateHCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 59733402Methyl 2-(2-(pyrrolidin-1-yl)ethoxy)benzoateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of triphenylphosphine (0.79 g, 3.0 mmol) in THF (15 ml) was successively added diisopropylazodicarboxylate (0.61 g, 3.0 mmol) followed by methyl salicylate (0.46 g, 3.0 mmol) and the resultant mixture stirred at ambient temperature for 1 h. 1-(2-Hydroxyethyl)-pyrrolidine (0.35 g, 3.0 mmol) was then added drop-wise and the reaction mixture left stirring at ambient temperature for a further 5 h. The reaction mixture was reduced in vacuo and purified by flash column chromatography [SiO2, EtOAc/MeOH (3:1, 1:1)] to give 2-(2-pyrrolidin-1-yl-ethoxy)-benzoic acid methyl ester as a clear yellow oil (446 mg, 60%). (LC/MS: Rt 1.58, [M+H]+ 250.05).

Workup

  1. waitthe reaction mixture left
  2. custompurified by flash column chromatography [SiO2, EtOAc/MeOH (3:1, 1:1)]

Sources & evidence

ORD record
ord-e9d611612a814ed88d4802ef9c48b1c3
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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