Hydrochloric Acid → 4-Hydroxymethyl-2-((Z)-2-tritylthioethen-1-yl)thiazole

HRID 2246081Notes

Reaction equation

HRID 2246081 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7](/[CH:10]=[CH:11]\[S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.O.Cl>ClCCl>[OH:2][CH2:3][C:5]1[N:6]=[C:7](/[CH:10]=[CH:11]\[S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 686011224-methoxycarbonyl-2-((Z)-2-tritylthioethen-1-yl)thiazoleHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 686009804-Hydroxymethyl-2-((Z)-2-tritylthioethen-1-yl)thiazoleYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.48 g of 4-methoxycarbonyl-2-((Z)-2-tritylthioethen-1-yl)thiazole in 70 ml of dichloromethane was cooled in ice, and 18.7 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 the same temperature for one hr. Water was then 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. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 2.88 g 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
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c6ee61b7b8664ebebe69616300b2c2ad
Source dataset
uspto-grants-2010_03
Patent number
US07687490B2

Reaction notes

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