HCID 67050187, compound → 2-(4-t-Butylphenyl)-3-methoxymethyloxy-4-methylcarbonylthiophene

HRID 1881534Notes

Reaction equation

HRID 1881534 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([CH:20]([OH:22])[CH3:21])[C:15]=2[O:16][CH2:17][O:18][CH3:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:20]([CH3:21])=[O:22])[C:15]=2[O:16][CH2:17][O:18][CH3:19])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67050187HCID 67050187, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 670504632-(4-t-Butylphenyl)-3-methoxymethyloxy-4-methylcarbonylthiopheneYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-t-Butylphenyl)-3-methoxymethyloxy-4-(1-hydroxyethyl)thiophene (0.64 g, 2.0 mmol) in dichloromethane (13 mL) was stirred with celite (2.0 g) and pyridinium chlorochromate (0.86 g, 4.0 mmol) at room temperature for 1 hour. The reaction solution was filtered through celite, and the filtrate was concentrated and purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to give the desired product as a brown solid (0.53 g, yield 83%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a989e8d1302b4a91848d773f35e61fda
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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