Dichloromethane → HCID 12972351, compound

HRID 1278792Notes

Reaction equation

HRID 1278792 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH2:6]([C:13]1[S:14][C:15]([CH3:19])=[C:16]([CH3:18])[CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:20](Cl)(=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.ClCCl>O>[CH2:6]([C:13]1[S:14][C:15]([CH3:19])=[C:16]([CH3:18])[C:17]=1[C:20]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:29])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 102419632,3-Dimethyl-5-benzylthiophene

Product 1

HCID 12972351HCID 12972351, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tin tetrachloride (4.6 mL, 71.76 mmol) was added dropwise over a 10 minute period to a stirred, −78° C. solution of 2-benzyl-4, 5 -dimethylthiophene (6.6 g, 32.62 mmol), anisoyl chloride (5.90 g, 34.6 mmol) and dichloromethane (120 mL) under a dry nitrogen atmosphere. After 5 hours at −78° C., the reaction mixture was slowly warmed to room temperature over a 2 h period. The reaction mixture was added to water and extracted with ether. The ether extract was washed with sat. aq. sodium bicarbonate and brine. The solvent was removed and the resultant solid was triturated with ether to give the title compound as a off-white solid (9.62 g, 88%): mp 85-86° C.: NMR (CDCl3); δ 7.80 (ddd, J=8, 8, 1 Hz, 2H), 7.24-7.10 (m, 5H), 7.92 (ddd, J=8, 8, 1 Hz, 2H), 3.93 (s, 2H), 3.88 (s, 3H), 2.28 (s, 3H), 1.90 (s, 3H); MS (EI): 336 (100%, MI); Anal. Calc. for C21H20O2S: C, 74.97, H, 5.99, N, 0.00. Found: C, 75.11, H, 6.02, N, 0.05.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with sat. aq. sodium bicarbonate and brine
  4. customThe solvent was removed
  5. customthe resultant solid was triturated with ether

Sources & evidence

ORD record
ord-51576f5ecdad4eeabe86517ee6c1dd94
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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