Methanol → Ethyl 2-(5-fluorobenzofur-7-yl)acetate

HRID 1824958Notes

Reaction equation

HRID 1824958 reaction equation
C(O[CH:5]([C:11]1[C:19]2[O:18][CH:17]=[CH:16][C:15]=2[CH:14]=[C:13]([F:20])[CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)C.CN(C)P(N(C)C)(N(C)C)=O.CO.O1CCCC1.[I-].[Sm+2].[I-]>C(OCC)(=O)C>[F:20][C:13]1[CH:12]=[C:11]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:19]2[O:18][CH:17]=[CH:16][C:15]=2[CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 12679HexamethylphosphoramideHCID 22144811HCID 22144811, compoundHCID 178420694Diiodosamarium;oxolane

Product 1

HCID 22144764Ethyl 2-(5-fluorobenzofur-7-yl)acetateYield 96.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.43 gm (5.10 mMol) ethyl 2-acetoxy-2-(5-fluorobenzofur-7-yl)acetate, 7.31 gm (40.8 mMol) hexamethylphosphoramide, 0.20 gm (6.12 mMol) methanol, and 153 mL (15.3 mMol) samarium(II) iodide tetrahydrofuran complex (0.1 M in tetrahydrofuran) was stirred at room temperature under a nitrogen atmosphere for 15 minutes. The reaction mixture was then diluted 10 fold with ethyl acetate, washed with water, and concentrated under reduced pressure to provide 1.09 gm (96%) of the desired compound.

Workup

  1. washwashed with water
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-060516bb8b984a33acf33db8e6e212ea
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

Loading…