Cesium carbonate → (S)-[3-(3-Hydroxy-butoxy)phenyl]-acetic acid methyl ester

HRID 902691Notes

Reaction equation

HRID 902691 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.[OH:13][C@@H:14]([CH3:28])[CH2:15][CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCCCCC>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:16][CH2:15][C@@H:14]([OH:13])[CH3:28])[CH:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 39129Methyl 3-HydroxyphenylacetateHCID 13204325(S)-Toluene-4-sulfonic acid 3-hydroxybutyl ester

Product 1

HCID 68861762(S)-[3-(3-Hydroxy-butoxy)phenyl]-acetic acid methyl esterYield 44.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring solution of (3-hydroxy-phenyl)-acetic acid methyl ester (0.93 g, 0.0056 mole) and toluene-4-sulfonic acid-(S)-3-hydroxy-butyl ester (1.5 g, 0.0061 mole) in anhydrous DMF (10 mL) was added Cs2CO3 (2.0 g, 0.006 mole). The reaction was heated to 100° C. and stirred for 4 hours. The mixture was cooled to RT and filtered. The filtrate was poured into H2O (50 mL) and extracted three times with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The crude product was subjected to column chromatography over silica gel (silica gel 60, EM Science) using 30% EtOAc:hexane as eluent to afford 0.59 g (44% yield) of the title compound as an oil: MS (ESI) 239.0 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered
  3. additionThe filtrate was poured into H2O (50 mL)
  4. extractionextracted three times with EtOAc
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-43bf11a3736c492a8be5fb2e16ce6af1
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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