Lithium Hydroxide → 4-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid

HRID 490338Notes

Reaction equation

HRID 490338 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1[O:8][C:9]([CH3:26])=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:11]=1)=[O:6]>O1CCCC1.CO>[C:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]2[CH:11]=[C:7]([C:5]([OH:6])=[O:4])[O:8][C:9]=2[CH3:26])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 588241734-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Product 1

HCID 7868594-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acidYield 22%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous lithium hydroxide (18 mL) was added to solution of 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (17) (1 g) in tetrahydrofuran/methanol (2:1 by volume, 100 mL) and the mixture stirred at room temperature for 5 h. The solvent was removed in vacuo, the residue dissolved in water (20 mL) and the solution acidified to pH6 with aqueous dilute hydrochloric acid. The mixture was evaporated to dryness and the residue was purified by HPLC to afford compound 18 as a white solid (210 mg). LC/MS System B: Rt=4.80 mins, m/z=307 ((M−1) for C19H16O4).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water (20 mL)
  3. customThe mixture was evaporated to dryness
  4. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-fdae456282f24099b3ef677fb8c0278a
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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