Cyclohexene ethanol → 2-Phenylbenzothiazol-5-ol

HRID 22710Notes

Reaction equation

HRID 22710 reaction equation
[C:1]1([C:7]2[S:8][C:9]3[CH:15]=[CH:14][C:13]([O:16]CC4C=CC=CC=4)=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.C1CCCCC=1>[OH-].[Pd+2].[OH-]>[C:1]1([C:7]2[S:8][C:9]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 18676862Cyclohexene ethanolHCID 22591632HCID 22591632, compound

Product 1

HCID 225916142-Phenylbenzothiazol-5-ol

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

Palladium hydroxide (100 mg) was added to a solution of 27 (260 mg, 0.8 mmol) of ethanol/cyclohexene (5 mL/2 mL) followed by warming for reflux for 16 h. The reaction mixture was cooled and the catalyst was removed by filtration (through Celite). The solvent was evaporated to provide compound 29 as a white solid. Synthesis of 5-(oxiran-2-ylmethoxy)-2-phenylbenzothiazole (59):

Workup

  1. temperatureby warming
  2. temperaturefor reflux for 16 h
  3. temperatureThe reaction mixture was cooled
  4. customthe catalyst was removed by filtration (through Celite)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1f01c3b8252b4b49bf46ef3a82e2dde9
Source dataset
uspto-grants-2005_02
Patent number
US06849632B2

Reaction notes

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