Hydrochloric Acid → HCID 136045961, compound

HRID 843151Notes

Reaction equation

HRID 843151 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[O:12][C:13]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21]CC=C)[C:14]=3[C:15]=2[CH3:16])[S:9][CH:10]=1)=[O:5])[CH3:2].C1N2CCN(CC2)C1.Cl>C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[O:12][C:13]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:14]=3[C:15]=2[CH3:16])[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 53887906HCID 53887906, compound

Product 1

HCID 136045961HCID 136045961, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 702EthanolSolvent

Procedure

2-(4-Allyloxy-3-methyl-benzofuran-2-yl)-thiazole-4-carboxylic acid ethyl ester (28 mg) in 80% aqueous ethanol (6 ml) was stirred in the presence of chlorotris(triphenylphosphine)rhodium (3 mg) and triethylenediamine (2 mg) at 90° C. for 6 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave 2-(4-hydroxy-3-methyl-benzofuran-2-yl)-thiazole-4-carboxylic acid ethyl ester as a white solid (21 mg). FAB-MS: m/z 304 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b8cae657f3cf4449ba2ab910484a972a
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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