Hydrochloric Acid → HCID 87511348, compound

HRID 1799697Notes

Reaction equation

HRID 1799697 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[Si:18]([O:25][CH2:26][C:27]1[S:31][CH:30]=[N:29][C:28]=1[C:32](OCC)=[O:33])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].O.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Si:18]([O:25][CH2:26][C:27]1[S:31][CH:30]=[N:29][C:28]=1[CH:32]=[O:33])([C:21]([CH3:24])([CH3:22])[CH3:23])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 68599910HCID 68599910, compoundHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 87511348HCID 87511348, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.0 M diisobutylaluminum hydride/toluene solution (2.4 ml) was added dropwise to a solution of 578 mg of 5-t-butyldimethylsilyloxymethyl-4-ethoxycarbonylthiazole in 10 ml of toluene under an argon atmosphere at −60° C. The mixture was stirred at the same temperature for 2 hr, water and ethyl acetate were added thereto and the mixture was adjusted to pH 5.5 by the addition of 1 N aqueous hydrochloric acid. The insolubles were removed by filtration through Celite, and the filtrate was extracted twice with ethyl acetate. The organic layers were combined, were washed with brine, were dried over anhydrous magnesium sulfate, were filtered, and were concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to ethyl acetate only) to give 308 mg of 5-t-butyldimethylsilyloxymethyl-4-formylthiazole.

Workup

  1. customThe insolubles were removed by filtration through Celite
  2. extractionthe filtrate was extracted twice with ethyl acetate
  3. washwere washed with brine
  4. dry with materialwere dried over anhydrous magnesium sulfate
  5. filtrationwere filtered
  6. concentrationwere concentrated under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-a21df76d88a942929953edc781bb68b6
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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