Ethyl Acetate → HCID 23449153, compound

HRID 1839284Notes

Reaction equation

HRID 1839284 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].[C:30]([C:35]1[N:36]=[CH:37][N:38]2[CH:42]=[CH:41][S:40][C:39]=12)(=[O:34])[CH:31]([CH3:33])[CH3:32].C(OCC)(=O)C>C1COCC1>[C:30]([C:35]1[N:36]=[CH:37][N:38]2[CH:42]=[C:41]([Sn:20]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:17][CH2:18][CH3:19])[S:40][C:39]=12)(=[O:34])[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 15096Tributyltin ChlorideHCID 23449121HCID 23449121, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23449153HCID 23449153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (12 ml) was added to 60 ml of THF. Tri-n-butylstannyl chloride (2.36 ml) and a solution of 1.18 g of 7-isobutyrylimidazo[5,1-b]thiazole in 1.18 ml of THF were added dropwise thereto in an argon atmosphere at −68° C. The mixture was stirred at the same temperature for one hr. Ethyl acetate (450 ml) was added to the reaction solution, and the mixture was washed with 200 ml of brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2) to give 1.55 g of the title compound.

Workup

  1. customat −68° C
  2. washthe mixture was washed with 200 ml of brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-2d16f6018ca94ad4943dabbe96c5260d
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

Loading…