Hydrochloric Acid → 4-(4-Iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acid

HRID 1786573Notes

Reaction equation

HRID 1786573 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([CH3:19])=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=2)[CH:9]=1)=[O:4].[OH-].[Li+].Cl>O1CCCC1.O>[I:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[O:6][C:7]=2[CH3:19])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 588241574-(4-Iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Product 1

HCID 184446544-(4-Iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acidYield 70.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-(4-iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (20) (2.7 g) in tetrahydrofuran (25 mL) was treated with a solution of lithium hydroxide (1.5 g) in water (2 mL). After 3 hours the reaction mixture was diluted with water and acidified to pH 2 with 1.0 M hydrochloric acid. The white precipitate was filtered off and dried in vacuo. The solid was triturated with ethyl acetate at 0° C. then collected by filtration to give compound 26 as a white solid (1.83 g). LC/MS system A: Rt=1.74 min.

Workup

  1. filtrationThe white precipitate was filtered off
  2. customdried in vacuo
  3. customThe solid was triturated with ethyl acetate at 0° C.
  4. filtrationthen collected by filtration

Sources & evidence

ORD record
ord-01f9e44084024917a8d3449096b9c05f
Source dataset
uspto-grants-2009_03
Patent number
US07507754B2

Reaction notes

Loading…