Diethyl Ether → HCID 11270004, compound

HRID 1359534Notes

Reaction equation

HRID 1359534 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][S:13][C:12]=2[C:22]([O:24][CH3:25])=[O:23])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:10])=O.[C:26]([O-:29])(=[O:28])[CH3:27].[Na+].C(OCC)C>C(OC(=O)C)(=O)C>[C:26]([O:29][CH2:10][S:8][C:7]1[CH:6]=[CH:5][C:4]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][S:13][C:12]=2[C:22]([O:24][CH3:25])=[O:23])=[CH:3][C:2]=1[F:1])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 11280269HCID 11280269, compound

Product 1

HCID 11270004HCID 11270004, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The methyl 3-[3-fluoro-4-(methylsulfinyl)phenyl]-4-phenyl-2-thiophenecarboxylate (4.13 g, 11.04 mmol) was dissolved in acetic anhydride (45.0 mL). Powdered sodium acetate (4.0 g, 48.7 mmol) was added and the solution was refluxed for 8 hours. The solution was poured into a 500 mL round bottom flask and solvent removed at reduced pressure. The residue was taken up in ethyl acetate (200 ml) and dichloromethane (20 mL). The solution was extracted with saturated sodium bicarbonate (3×100 mL) followed by saturated ammonium chloride (2×100 mL). The solvent was removed at reduce pressure and residue taken up in ether, dried over sodium sulfate and solvent removed at reduced pressure. Methyl 3-[4-[[(acetyloxy)methyl]thio]-3-fluorophenyl]-4-phenyl-2-thiophenecarboxylate (2.9 g, 6.90 mmol) was isolated by crystallization from diethyl ether and hexanes as white crystals. (62% yield). Mp 102.9-103.7° C. 1H NMR (CDCl3/300 MHz) 7.53 (s, 1H), 7.43 (t, 1H, J=7.8 Hz), 7.22-7.28 (m, 3H), 7.04-7.08 (m, 2H), 6.92-6.98 (m, 2H), 5.42 (s, 2H), 3.81 (s, 3H), 2.11 (s, 3H). ESHRMS m/z 434.0898 (calcd for M+NH4+, 434.0896)

Workup

  1. temperaturethe solution was refluxed for 8 hours
  2. additionThe solution was poured into a 500 mL round bottom flask
  3. customsolvent removed at reduced pressure
  4. extractionThe solution was extracted with saturated sodium bicarbonate (3×100 mL)
  5. customThe solvent was removed
  6. dry with materialdried over sodium sulfate and solvent
  7. customremoved at reduced pressure

Sources & evidence

ORD record
ord-783b68ada0854de1a166fcaccef67f07
Source dataset
uspto-grants-2003_07
Patent number
US06600052B1

Reaction notes

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