HCID 86644410, compound → HCID 86644411, compound

HRID 2194677Notes

Reaction equation

HRID 2194677 reaction equation
[OH:1][CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]1[S:7][C:6]([CH2:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[C:2]([C:3]1[S:7][C:6]([CH2:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[CH:5][C:4]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:1])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 86644410HCID 86644410, compound

Product 1

HCID 86644411HCID 86644411, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of tert-butyl ({5-[hydroxy(phenyl)methyl]-4-phenyl-2-thienyl}methyl)methylcarbamate (385 mg) in toluene (5 mL) was added manganese dioxide (1.1 g) and the mixture was stirred at 120° C. for 8 hr. The reaction mixture was cooled to room temperature, filtered through celite, and washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as a pale-yellow oil (yield 236 mg, yield 62%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-e1812ee9acee4980b319ab69950a1ae4
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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