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Acetyl chloride → Acetic acid 4-acetyl-2-(4-tert-butylphenyl)thiophen-3-yl ester

HRID 1881651
Notes
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Reaction equation

HRID 1881651 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:17]([CH3:19])=[O:18])[C:15]=2[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>C1COCC1>[C:17]([C:14]1[C:15]([O:16][C:27](=[O:29])[CH3:28])=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=2)[S:12][CH:13]=1)(=[O:18])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 442072892-(4-t-Butylphenyl)-3-hydroxy-4-methylcarbonylthiophene

Product 1

HCID 67050465Acetic acid 4-acetyl-2-(4-tert-butylphenyl)thiophen-3-yl esterYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-tert-butylphenyl)-3-hydroxy-4-methylcarbonylthiophene (137 mg, 0.5 mmol) in THF (2 mL) were added triethylamine (105 μL, 0.75 mmol) and acetyl chloride (53.3 μL, 0.75 mmol). The reaction mixture was stirred at room temperature for 0.5 h. After removing solvent, the residue was diluted with AcOEt, washed with a saturated aqueous NH4Cl solution, dried over MgSO4 and concentrated to give product as a brown oil (146 mg, yield 92%).

Workup

  1. customAfter removing solvent
  2. additionthe residue was diluted with AcOEt
  3. washwashed with a saturated aqueous NH4Cl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8572ba24a8604ba19ce6c17ab5c7304b
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318796B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes