Ethanol → (RS)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl ester

HRID 1247438Notes

Reaction equation

HRID 1247438 reaction equation
[CH2:1]([O:3][CH:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[F:16])[C:5]([OH:7])=[O:6])[CH3:2].[CH2:17](O)[CH3:18].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.ClCCl>[CH2:17]([O:6][C:5](=[O:7])[CH:4]([O:3][CH2:1][CH3:2])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[F:16])[CH3:18]

Participants

6

Reactant 3

HCID 702EthanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 21904991(RS)-Ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid

Product 1

HCID 69290014(RS)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (RS)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid (7.26 g, example 63.1), ethanol (16.7 ml) and DMAP (1.57 g) in dichloromethane (120 ml) was cooled to 0° and treated with EDCI (6.59 g). The reaction stirred was stirred at rt for 18 hrs, then washed with 0.5 N HCl, H2O, saturated NaHCO3 and brine. The organic layer was dried over MgSO4, filtrated and concentrated. The crude product was purified by flash chromatography (cyclohexane=>cyclohexane/EtOAc 85:15) to give (RS)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl ester (4.42 g) as yellow oil. MS 256.2 ([M]+)

Workup

  1. stirringwas stirred at rt for 18 hrs
  2. washwashed with 0.5 N HCl, H2O, saturated NaHCO3 and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (cyclohexane=>cyclohexane/EtOAc 85:15)

Sources & evidence

ORD record
ord-95fe4e6d0ca0468a9c09b97b6eac921f
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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