Carbon Disulfide → HCID 10831160, compound

HRID 1873217Notes

Reaction equation

HRID 1873217 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH2:6]([C:13]1[O:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:22](Cl)(=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.C(=S)=S>O>[CH2:6]([C:13]1[O:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[C:17]=1[C:22]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:31])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 12218409HCID 12218409, compound

Product 1

HCID 10831160HCID 10831160, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tin tetrachloride (6.5 mL, 55.5 mmol) was added dropwise over a 30 minute period to a stirred solution of 2-benzyl-benzofuran (10.0 g, 48.01 mmol), anisoyl chloride (8.51 g, 49.93 mmol) and carbon disulfide (53 mL) at room temperature under a dry nitrogen atmosphere. After 15 h the reaction mixture was added to water and extracted with dichloromethane. Silica gel was added to the dichloromethane phase and the solvent was removed. The adsorbate was flash chromatographed (95:5 petroleum ether:ethyl acetate as eluent) to provide the title compond as a white solid (13.84 g, 84%): mp 84-85° C.: NMR (CDCl3); δ7.87 (dm, J=9 Hz, 2 H), 7.46 (dm, 1 H), 7.36-7.12 (m, 8 H), 6.97 (dm, J=9 Hz, 2 H), 4.29 (s, 2 H), 3.90 (s, 3 H): MS (EI):

Workup

  1. extractionextracted with dichloromethane
  2. additionSilica gel was added to the dichloromethane phase
  3. customthe solvent was removed
  4. customchromatographed (95:5 petroleum ether:ethyl acetate as eluent)

Sources & evidence

ORD record
ord-d2e5ea0c080245f489b8580b112b73ee
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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