Acetic Anhydride → HCID 67486354, compound

HRID 2371259Notes

Reaction equation

HRID 2371259 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([CH:24]=O)=[CH:22][CH:23]=1)=[O:18].C(OC(=O)C)(=O)C.C(N(CC)CC)C>O.C(O)(=O)C>[CH3:15][O:16][C:17]([C:19]1[S:20][C:21](/[CH:24]=[C:11](\[C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)/[C:12]([OH:14])=[O:13])=[CH:22][CH:23]=1)=[O:18]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 118343Benzeneacetic acid, 4-(1,1-dimethylethyl)-HCID 818924Methyl 5-formylthiophene-2-carboxylate

Product 1

HCID 67486354HCID 67486354, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

To (4-tert-butyl-phenyl)-acetic acid (1.15 g, 6.0 mmol) was added 5-formyl-thiophene-2-carboxylic acid methyl ester (1 g, 5.7 mmol), acetic anhydride (3.08 g, 30.2 mmol), and triethyl amine (574 mg, 5.7 mmol). The resulting mixture was stirred at 120° C. for 16 hours and cooled down. Water (1.9 ml) was added. The reaction mixture was heated up to 100° C. for 5 minutes in microwave and cooled down to 23° C. A mixture of acetic acid and water (2.5 ml:2.5 ml) was added. The resulting reaction mixture was stirred at 23° C. for 1 hour. The precipitate was filtered off, washed with 25% aqueous acetic acid, then water. The solid was dried under high vacuum to afford 5-[(E)-2-(4-tert-Butyl-phenyl)-2-carboxy-vinyl]-thiophene-2-carboxylic acid methyl ester as a brownish solid (1.32 g, 67%).

Workup

  1. temperaturecooled down
  2. temperatureThe reaction mixture was heated up to 100° C. for 5 minutes in microwave
  3. temperaturecooled down to 23° C
  4. additionwas added
  5. customThe resulting reaction mixture
  6. stirringwas stirred at 23° C. for 1 hour
  7. filtrationThe precipitate was filtered off
  8. washwashed with 25% aqueous acetic acid
  9. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-308e695ca1ce4f70bbf7d511557d7642
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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