Hexane → HCID 19878442, compound

HRID 728796Notes

Reaction equation

HRID 728796 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 extractedtwice with water and then three times using 200 ml of 5% soda solution eachtime. 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##

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. additionare added
  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. filtrationThe alkaline phase is filtered
  11. additionpoured onto ice and 2N hydrochloric acid
  12. customthe crystals that are formed
  13. filtrationare filtered off
  14. customdried
  15. customChromatography over silica gel and recrystallisation from methanol

Sources & evidence

ORD record
ord-f27c9a54749440a5b6c384bae5925368
Source dataset
uspto-grants-1991_09
Patent number
US05051421

Reaction notes

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