Lithium Hydroxide → HCID 71743897, compound

HRID 2401485Notes

Reaction equation

HRID 2401485 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[C:9]2[CH:10]=[C:11]([C:13]([O:15]C)=[O:14])[O:12][C:8]=2[CH:7]=[C:6]([N+:17]([O-:19])=[O:18])[C:5]=1[O:20][CH3:21]>CO.O>[Cl:3][C:4]1[C:9]2[CH:10]=[C:11]([C:13]([OH:15])=[O:14])[O:12][C:8]=2[CH:7]=[C:6]([N+:17]([O-:19])=[O:18])[C:5]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 14916653HCID 14916653, compound

Product 1

HCID 71743897HCID 71743897, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Lithium hydroxide (0.9 g, 21.0 mmol) was added to a stirred suspension of methyl 4-chloro-5-methoxy-6-nitrobenzofuran-2-carboxylate (2.0 g, 7.0 mmol) in methanol-water (3:1) (40 mL). The reaction was allowed to stir for 3 h at room temperature. The reaction was then concentrated under reduced pressure and the resulting residue was dissolved in water and washed with diethyl ether. The aqueous phase was acidified by the addition of 2M aqueous hydrochloric acid then extracted with ethyl acetate. The combined organic extracts were passed through a phase separation cartridge and evaporated to afford a white solid (1.17 g, 61%), which was taken through to the next step with no further purification.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water
  3. washwashed with diethyl ether
  4. additionThe aqueous phase was acidified by the addition of 2M aqueous hydrochloric acid
  5. extractionthen extracted with ethyl acetate
  6. customThe combined organic extracts were passed through a phase separation cartridge
  7. customevaporated

Sources & evidence

ORD record
ord-46c2ebbd93144a3898fc48a5957d6849
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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