Triethylamine → 4-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl-ethynyl)thiazole

HRID 993001Notes

Reaction equation

HRID 993001 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]2[S:16][CH:17]=[C:18]([C:20](O)=[O:21])[N:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(OCC)=O>C1COCC1>[OH:21][CH2:20][C:18]1[N:19]=[C:15]([C:14]#[C:13][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[S:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 184085032-(3,4,5-Trimethoxyphenylethynyl)thiazole-4-carboxylic Acid

Product 1

HCID 184084964-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl-ethynyl)thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3,4,5-Trimethoxyphenylethynyl)thiazole-4-carboxylic acid (133 mg) was dissolved in THF (8 mL), and to the solution triethylamine (44 mg) was added, and ethyl chloroformate (48 mg) was then added at 0° C. to stir the mixture for 15 minutes. The reaction mixture was filtered, an aqueous solution (2 mL) of sodium borohydride (16 mg) was added to the filtrate, and the resultant mixture was stirred for 30 minutes. Water was added to the reaction mixture, the resultant mixture was extracted with ethyl acetate. The resultant organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After concentrating the organic layer under reduced pressure, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to 1:2) to obtain the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionan aqueous solution (2 mL) of sodium borohydride (16 mg) was added to the filtrate
  3. stirringthe resultant mixture was stirred for 30 minutes
  4. additionWater was added to the reaction mixture
  5. extractionthe resultant mixture was extracted with ethyl acetate
  6. washThe resultant organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationAfter concentrating the organic layer under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to 1:2)

Sources & evidence

ORD record
ord-cfb8329e11a7418b81d6cdcec87dec5c
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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