Methanol → HCID 20306083, compound

HRID 1732327Notes

Reaction equation

HRID 1732327 reaction equation
[CH3:1][Li].[Cl:3][C:4]1[C:15]([C:16](=[O:22])[C:17]2[S:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:7]2[CH2:8][CH:9]([C:11](Cl)=[O:12])[O:10][C:6]=2[C:5]=1[Cl:23].CO.[Cl-].[NH4+]>>[C:11]([CH:9]1[CH2:8][C:7]2[CH:14]=[C:15]([C:16](=[O:22])[C:17]3[S:21][CH:20]=[CH:19][CH:18]=3)[C:4]([Cl:3])=[C:5]([Cl:23])[C:6]=2[O:10]1)(=[O:12])[CH3:1]

Participants

5

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 20306079HCID 20306079, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20306083HCID 20306083, compound

Conditions

Temperature
0 °C

Procedure

Cuprous iodide (5.7 g., 0.03 mole) is placed in a 250 ml. three-necked round-bottom flask equipped with a magnetic stirring bar, septum stopper, nitrogen inlet and CaSO4 drying tube. The flask is flame dried while purging it with nitrogen. Diethyl ether (80 ml.) is added and the flask is cooled to 0° C. Methyl lithium (42.8 ml. of 1.4 M solution, 0.06 mole) is added to the stirred mixture. After ten minutes at 0° C. the temperature is lowered to -78° C. A cooled etheral solution (25 ml.) of 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carbonyl chloride (3.6 g., 0.01 mole) is added. After stirring 15 minutes at -b 78° C., the reaction is quenched by adding methanol (3.52 g., 0.011 mole). The reaction mixture is allowed to warm up to 25° C. and then is poured into 150 ml. of saturated aqueous ammonium chloride. The mixture is extracted with ether (3×50 ml.). The ether extracts are combined, dried over MgSO4 and evaporated in vacuo to give 2-acetyl-6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran.

Workup

  1. customthree-necked round-bottom flask equipped with a magnetic stirring bar
  2. temperatureThe flask is flame
  3. customdried
  4. customwhile purging it with nitrogen
  5. additionDiethyl ether (80 ml.) is added
  6. waitAfter ten minutes at 0° C. the temperature is lowered to -78° C
  7. customthe reaction is quenched
  8. temperatureto warm up to 25° C.
  9. additionis poured into 150 ml
  10. extractionThe mixture is extracted with ether (3×50 ml.)
  11. dry with materialdried over MgSO4
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-5ce41cbc0da14f9a8413af884afe4d07
Source dataset
uspto-grants-1980_12
Patent number
US04237144

Reaction notes

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