Acetic Anhydride → HCID 15078744, compound

HRID 359153Notes

Reaction equation

HRID 359153 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][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([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:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15078743HCID 15078743, compound

Product 1

HCID 15078744HCID 15078744, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

3-Hydroxy-2-(4'-methoxyphenyl)-5-phenylthiophene (200 mg, 0.71 mmol) was dissolved in 2.0 mL of pyridine and treated with acetic anhydride (0.50 mL, 5.3 mmol). The solution was stirred 4 hours at 25° C., and then most of the acetic anhydride and pyridine were removed on a rotary evaporator at reduced pressure. The residue was dissolved in 40 mL of ethyl acetate and washed with 2×15 mL of 2N aqueous hydrochloric acid, 15 mL of saturated aqueous sodium bicarbonate, and 15 mL of saturated aqueous sodium chloride. The solution was dried over sodium sulfate, decanted, and evaporated. The residual oil (224 mg) began to crystallize upon standing overnight. This was combined with other material prepared by the same method and recrystallized twice from 3-4 mL of 7% ethyl acetate in hexane to give 3-acetoxy-2-(4'-methoxyphenyl)-5-phenylthiophene as very pale pink needles, m.p. 81°-82° C.

Workup

  1. custommost of the acetic anhydride and pyridine were removed on a rotary evaporator at reduced pressure
  2. dissolutionThe residue was dissolved in 40 mL of ethyl acetate
  3. washwashed with 2×15 mL of 2N aqueous hydrochloric acid, 15 mL of saturated aqueous sodium bicarbonate, and 15 mL of saturated aqueous sodium chloride
  4. dry with materialThe solution was dried over sodium sulfate
  5. customdecanted
  6. customevaporated
  7. customto crystallize
  8. waitupon standing overnight
  9. customprepared by the same method
  10. customrecrystallized twice from 3-4 mL of 7% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2dc44a1ce3e14cfc877f6286ef228de6
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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