Tetrahydrofuran → HCID 19605103, compound

HRID 1603499Notes

Reaction equation

HRID 1603499 reaction equation
C([Al]CC(C)C)C(C)C.C1COCC1.C([O:17][C:18]([C:20]1[S:24][C:23]2=[CH:25][N:26]=[CH:27][N:22]2[C:21]=1[C:28](OCC)=[O:29])=O)C>C(OCC)C.O>[OH:17][CH2:18][C:20]1[S:24][C:23]2=[CH:25][N:26]=[CH:27][N:22]2[C:21]=1[CH2:28][OH:29]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 16682954DibahHCID 19605035HCID 19605035, compound

Product 1

HCID 19605103HCID 19605103, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A 1.33 ml potion of a 1.5M diisobutylaluminum hydridetoluene solution was added dropwise to 5 ml of an anhydrous THF solution containing 268 mg of 2,3-bis(ethoxycarbonyl)imidazo[5,1-b]thiazole in an argon atmosphere at -78° C., and the mixture was then stirred at the same temperature for 1 hour. Then, the reaction solution was diluted with 5 ml of diethyl ether, and 1.5 ml of water was then added thereto. After stirred at room temperature for 2 hours, the solution was filtered through Celite. The filtrate was dried over anhydrous magnesium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 148 mg of the title compound as a colorless crystal.

Workup

  1. additionwas then added
  2. stirringAfter stirred at room temperature for 2 hours
  3. filtrationthe solution was filtered through Celite
  4. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-827ef425c2b34ecc8fe42282cf285d97
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

Loading…