Hexane → HCID 19878442, compound

HRID 1885904Notes

Reaction equation

HRID 1885904 reaction equation
[S:1]1[C:5](=[O:6])[CH2:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.[H-].[Na+].CCCCCC.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24][C:25](Cl)=[O:26]>O=P(N(C)C)(N(C)C)N(C)C>[OH:6][C:5]1[S:1][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]=1[C:25](=[O:26])[CH2:24][C:20]1[S:19][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 1623622-Thiopheneacetyl chlorideHCID 591560Benzo[b]thiophen-2(3H)-one

Product 1

HCID 19878442HCID 19878442, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

In a sulfonating flask under a nitrogen atmosphere, 15 g of benzo[b]thiophene-2(3H)-one (100 mmol) are dissolved in 150 ml of distilled hexametapol. The light-yellow solution is cooled to 5°. 8.9 g of a sodium hydride suspension (55%) that has been de-oiled with n-hexane are then added in portions while stirring. The resulting suspension is stirred for 15 minutes at 20°, during which time the evolution of gas is observed. The suspension is then cooled to -10° and 17.65 g of 2-(2-thienyl)-acetic acid chloride are added, the internal temperature being maintained at below 0°. After the cooling has been removed, the mixture is stirred for 1 hour. The reaction mixture is poured onto 2 liters of ice-water and 60 ml of 2N hydrochloric acid, and then 500 ml of toluene are added. The separated organic phase is extracted twice with water and then three times using 200 ml of 5% soda solution each time. The alkaline phase is filtered and poured onto ice and 2N hydrochloric acid, and the crystals that are formed are filtered off and dried. Chromatography over silica gel and recrystallisation from methanol yield 2-hydroxy-3-[2-(2-thienyl)-acetyl]-benzo[b]thiophene, ##STR7## m.p. 99°-101°, which is digested in 100 ml of methanol, and 13.68 ml of 30% sodium methanolate solution are added. After concentration to dryness by evaporation, first 200 ml of ether and then acetone are added. The crystalline sodium salt melts at 201°-204°.

Workup

  1. temperatureThe light-yellow solution is cooled to 5°
  2. additionare then added in portions
  3. stirringThe resulting suspension is stirred for 15 minutes at 20°, during which time the evolution of gas
  4. temperatureThe suspension is then cooled to -10°
  5. temperaturethe internal temperature being maintained at below 0°
  6. customAfter the cooling has been removed
  7. stirringthe mixture is stirred for 1 hour
  8. additionThe reaction mixture is poured onto 2 liters of ice-water and 60 ml of 2N hydrochloric acid
  9. addition500 ml of toluene are added
  10. extractionThe separated organic phase is extracted twice with water
  11. filtrationThe alkaline phase is filtered
  12. additionpoured onto ice and 2N hydrochloric acid
  13. customthe crystals that are formed
  14. filtrationare filtered off
  15. customdried
  16. customChromatography over silica gel and recrystallisation from methanol

Sources & evidence

ORD record
ord-9c1f8448795b4dd2b194eb87843471f0
Source dataset
uspto-grants-1992_09
Patent number
US05147889

Reaction notes

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