Acetic Anhydride → HCID 15078749, compound

HRID 359156Notes

Reaction equation

HRID 359156 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C(N(CC)CC)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(#N)C.CN(C)C1C=CN=CC=1>[C:27]([O:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 15078748HCID 15078748, compound

Product 1

HCID 15078749HCID 15078749, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

3-Hydroxy-2-(2-methylphenyl)-5-phenylthiophene (537 mg, 2.02 mmol) was dissolved in acetonitrile (4.0 mL), and 4-dimethylaminopyridine (15 mg, 0.12 mmol) and triethylamine (0.65 mL, 470 mg, 6.9 mmol) were added followed by acetic anhydride (0.65 mL, 700 mg, 6.9 mmol). The reaction was stirred overnight at 25° C. The reaction mixture was evaporated and the residue was chromatographed on 30 g of silica gel eluting with 700 mL of 15% ethyl acetate in hexane. 3-Acetoxy-2-(2'-methylphenyl)-5-phenylthiophene was isolated as 370 mg of viscous oil. The product could be distilled bulb-to-bulb, bp (0.4 mm) 140°-150° C.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on 30 g of silica gel eluting with 700 mL of 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8026e635086f4db6a067bf8287b8921f
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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