Hydrochloric Acid → HCID 68601127, compound

HRID 1799692Notes

Reaction equation

HRID 1799692 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9](/[CH:11]=[CH:12]\[S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.O.Cl>C1COCC1>[OH:3][CH2:4][C:6]1[S:10][C:9](/[CH:11]=[CH:12]\[S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 68601909HCID 68601909, compoundHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 68601127HCID 68601127, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 257 mg of 5-ethoxycarbonyl-2-((Z)-2-tritylthioethen-1-yl)thiazole in 10 ml of THF was cooled in ice, and 1.69 ml of a 1.0 M diisobutylaluminum hydride/toluene solution was added dropwise to the cooled solution under an argon atmosphere. The mixture was stirred at room temperature for 2 hr. Water was added to the reaction solution, and the mixture was adjusted to pH 2.5 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 to give 234 mg of the title compound.

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

Sources & evidence

ORD record
ord-d77b1d9c92994793b2ea3b72ff0b191e
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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