Tetrahydrofuran → HCID 57742154, compound

HRID 1626877Notes

Reaction equation

HRID 1626877 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1)[CH3:2].[H-].[Na+].C1[CH2:20][O:19][CH2:18]C1>O>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:18][O:19][CH3:20])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 572437Ethyl (3-Hydroxyphenyl)acetate

Product 1

HCID 57742154HCID 57742154, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (3-Hydroxy-phenyl)-acetic acid ethyl ester (27.6 g) in THF was added NaH (7.35 g), MOM-CI (14.8 g) slowly at 0°. After stirred for 14 h at the same temperature, the reaction mixture was warmed to room temperature. The resulting mixture was diluted with water and extracted with EtOAc. The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=15:1 to 10:1) to afford the product as colorless oil. (31.2 g, 90.9%)

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=15:1 to 10:1)

Sources & evidence

ORD record
ord-bd90000b64a5472da79065627be4c63d
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

Loading…