Lithium hydroxide, monohydrate → HCID 66607809, compound

HRID 221145Notes

Reaction equation

HRID 221145 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([O:13]CC)=[O:12])[S:8][C:7]=2[CH:16]=1)[CH3:2].O.[OH-].[Li+]>O1CCCC1.CO>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[S:8][C:7]=2[CH:16]=1)[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66608263HCID 66608263, compound

Product 1

HCID 66607809HCID 66607809, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above 6-ethyl-2-ethoxycarbonylbenzo[b]thiophene (1.26 g) was dissolved in tetrahydrofuran (4 ml) and methanol (8 ml), and added thereto was lithium hydroxide monohydrate (677 mg), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in water and the solution was made acidic with a 10% aqueous hydrochloric acid solution. The precipitates were collected by filtration and washed with water to give 6-ethylbenzo[b]thiophen-2-ylcarboxylic acid (1.15 g) as colorless crystals. ESI-1-Mass m/Z 205 (M−H). (4) The above 6-ethylbenzo[b]thiophen-2-ylcarboxylic acid was tread in a manner similar to Reference Example 47-(2) to give the desired 6-ethylbenzo[b]thiophene as colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-f6c3596c1a654e638debf896fce3f6bf
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

Loading…