Ethyl Acetate → HCID 18360035, compound

HRID 382605Notes

Reaction equation

HRID 382605 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[CH:10][S:9][C:8]=12.C([Li])CCC.CCCCCC.[CH2:23]([Sn:27](Cl)([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26].C(OCC)(=O)C>C1COCC1>[CH3:1][O:2][CH2:3][C:4]1[N:5]=[CH:6][N:7]2[C:11]([Sn:27]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:10][S:9][C:8]=12

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 15096Tributyltin ChlorideHCID 18359932HCID 18359932, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 18360035HCID 18360035, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 925 mg of 7-methoxymethylimidazo[5,1-b]thiazole in anhydrous THF was cooled to −70° C. under the atmosphere of argon and 3.54 ml of a 1.6 N n-butyl lithium/n-hexane solution was slowly added, and the mixture was stirred for 1 hour. To the reaction mixture was slowly added a solution of 1.88 g of tri-n-butylstannyl chloride in 2 ml of anhydrous THF, and the mixture was stirred for further 1.5 hours. After the addition of 100 ml of ethyl acetate, the solvent was removed by distillation to concentrate the mixture to a total volume of about 1 ml. Purification by silica gel chromatography gave 896 mg of 7-methoxymethyl-3-(tri-n-butylstannyl)imidazo[5,1-b]thiazole from a low polar fraction eluted with dichloromethane:ethyl acetate=4:1.

Workup

  1. additionwas slowly added
  2. stirringthe mixture was stirred for further 1.5 hours
  3. customthe solvent was removed by distillation
  4. concentrationto concentrate the mixture to a total volume of about 1 ml
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-4f333982fbdf44dd8c705a039885676f
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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