Lithium hydroxide, monohydrate → 4-{4-[(Dimethylamino)carbonyl]phenoxy}-2-ethyl-1-benzofuran-6-carboxylic acid

HRID 1643742Notes

Reaction equation

HRID 1643742 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[CH:27]=[CH:26][C:8]([O:9][C:10]2[C:15]3[CH:16]=[C:17]([CH2:19][CH3:20])[O:18][C:14]=3[CH:13]=[C:12]([C:21]([O:23]CC)=[O:22])[CH:11]=2)=[CH:7][CH:6]=1)=[O:4].O[Li].O>CO.O>[CH3:28][N:2]([CH3:1])[C:3]([C:5]1[CH:27]=[CH:26][C:8]([O:9][C:10]2[C:15]3[CH:16]=[C:17]([CH2:19][CH3:20])[O:18][C:14]=3[CH:13]=[C:12]([C:21]([OH:23])=[O:22])[CH:11]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59560279Ethyl 4-{4-[(dimethylamino)carbonyl]phenoxy}-2-ethyl-1-benzofuran-6-carboxylate

Product 1

HCID 595601564-{4-[(Dimethylamino)carbonyl]phenoxy}-2-ethyl-1-benzofuran-6-carboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of ethyl 4-{4-[(dimethylamino)carbonyl]phenoxy}-2-ethyl-1-benzofuran-6-carboxylate (400 mg, 1.0 mmol) and LiOH.H2O (200 mg, 4.7 mmol) in MeOH (20 mL) and water (2 mL) was stir for 4 hr at room temperature. TLC (petroleum ether/EtOAc 4:1) indicated the reaction was complete. The reaction mixture was concentrated to dryness and poured into water (30 mL). The aqueous layer was acidified to pH˜2 with conc. HCl and extracted with EtOAc (20 mL×3). The organic layer was washed with brine (25 mL×2), dried over Na2SO4 and concentrated to afford the desired product (350 mg, 99%) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionpoured into water (30 mL)
  3. extractionextracted with EtOAc (20 mL×3)
  4. washThe organic layer was washed with brine (25 mL×2)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b35c82d1bc4a4018ab5536418e990f05
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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