Lithium Hydroxide → HCID 58227488, compound

HRID 2092963Notes

Reaction equation

HRID 2092963 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][CH:7]=1)=[O:5])C.[OH-].[Li+].O1CCCC1>O>[C:13]1([C:12]#[C:11][C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58227511HCID 58227511, compound

Product 1

HCID 58227488HCID 58227488, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-phenylethynyl-thiazole-5-carboxylic acid ethyl ester (9.00 g, 35.0 mmol), lithium hydroxide (13.5 g, 563 mmol), tetrahydrofuran (190 mL) and water (143 mL) was stirred at 25° C. for 64 h. The material was concentrated to remove most of the THF, taken up in 350 mL of water and washed with EtOAc (3×50 mL); acidified with 3.7% HCl to pH<1 and the precipitate extracted with 3×100 mL of EtOAc. The combined EtOAc extracts were washed with 50 mL of water, 50 mL of brine, dried (Na2SO4) and concentrated to give the titled compound, 2-phenylethynyl-thiazole-5-carboxylic acid (7.79 g; 97%), as a yellow powder, which was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 1H), 7.69-7.60 (m, 2H), 7.51-7.38 (m, 3H). LC/MS (Method 1), RT=0.57 min. Calculated [M+H]+=230; Observed [M+H]+=230.

Workup

  1. concentrationThe material was concentrated
  2. customto remove most of the THF
  3. washwashed with EtOAc (3×50 mL)
  4. extractionthe precipitate extracted with 3×100 mL of EtOAc
  5. washThe combined EtOAc extracts were washed with 50 mL of water, 50 mL of brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-785559c309c043b888baaa824d741b18
Source dataset
uspto-grants-2013_05
Patent number
US08440837B2

Reaction notes

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