p-Anisoyl chloride → HCID 9863606, compound

HRID 651482Notes

Reaction equation

HRID 651482 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[S:6]1[C:10]([CH2:11][C:12]2[O:16][C:15]([CH3:17])=[C:14]([CH3:18])[CH:13]=2)=[CH:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2.[C:23](Cl)(=O)[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>C(=S)=S>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]2[C:9]3[C:8]4[C:7](=[CH:22][CH:21]=[CH:20][CH:19]=4)[S:6][C:10]=3[CH:11]=[C:12]3[O:16][C:15]([CH3:17])=[C:14]([CH3:18])[C:13]=23)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 15550520HCID 15550520, compound

Product 1

HCID 9863606HCID 9863606, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
0 °C

Procedure

Tin tetrachloride (7.6 mL, 65.2 mmnol) was added dropwise to a −78° C., stirred solution of benzo[b]thiophen-2-yl-(2,3-dimethyl-furan-5-yl)-methane (3.96 g, 16.3 mmol) and anisoyl chloride (3.07 g, 17.93 mL) in carbon disulfide (100 mL) under a try N2 atmosphere over a period of 30 min. After the addition completed, the solution was allowed to warm to 0° C. After 9 h. the reaction mixture was carefully quenched with and further diluted with water (350 mL). Aqueous mixture was extracted with ethyl ether. The ethyl ether extracts were washed with water, 10% aqueous sodium bicarbonate and water and dried with brine. Silica gel (90 mL) was added. Solvents were removed and the silica adsorbate was flash chromatographed (eluent 99:1 petroleum ether:ethyl acetate) to provide the title compound as a light yellow solid (1.1 g, 25%): NMR (CDC13); δ 7.81 (s, 1H), 7.76 (d, J=8, Hz, 1H), 7.36-7.24 (m, 3H), 7.11-7.00 (m, 3H), 6.85 (d, J=8 Hz, 1H), 3.96 (s, 3H), 2.37 (s, 3H), 1.55 (s, 3H); MS (EI): [M+], 358.

Workup

  1. additionAfter the addition
  2. customAfter 9 h. the reaction mixture was carefully quenched with and
  3. additionfurther diluted with water (350 mL)
  4. extractionAqueous mixture was extracted with ethyl ether
  5. washThe ethyl ether extracts were washed with water, 10% aqueous sodium bicarbonate and water
  6. dry with materialdried with brine
  7. additionSilica gel (90 mL) was added
  8. customSolvents were removed
  9. customchromatographed (eluent 99:1 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-b08c004e2cf04625a2b91937348c0fa0
Source dataset
uspto-grants-2001_08
Patent number
US06281238B1

Reaction notes

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