Water → HCID 13961646, compound

HRID 1165587Notes

Reaction equation

HRID 1165587 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:8]1[C:9]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:10]=2[S:11][C:12]=1[C:13](Cl)=[O:14].[OH2:22]>O1CCCC1.CO.[OH-].[Na+]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:9]2[C:8]([O:4][CH:1]([CH3:3])[CH3:2])=[C:12]([C:13]([OH:22])=[O:14])[S:11][C:10]=2[CH:16]=1

Participants

8

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 125946383-Chloro-6-methoxy-1-benzothiophene-2-carbonyl chloride

Product 1

HCID 13961646HCID 13961646, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

Isopropanol (16.8 g, 280 mmoles) is added dropwise to a stirred suspension of sodium hydride (11.2 g of a 60% dispersion in mineral oil, 280 mmoles) in tetrahydrofuran (50 mls) under argon. After 20 minutes a solution of 3-chloro-6-methoxybenzo[b]thiophene-2-carbonyl chloride (24.2 g, 93 mmoles) in warm tetrahydrofuran (180 mls) is added gradually during 5 minutes, and the mixture is heated under reflux. After 16 hours the mixture is cooled and stripped of solvent under reduced pressure. The residue is partitioned between water (600 mls) and ether (300 mls). The layers are separated and the aqueous phase extracted twice with ether (200 mls). The combined ether extracts are washed with saturated brine, dried over MgSO4, and stripped of solvent under reduced pressure to leave the crude ester as syrup which also contains mineral oil. The syrup is stirred in a mixture of methanol (20 mls) and 1N sodium hydroxide (100 mls), and heated under reflux. After 12 hours the mixture is stirred into water (600 mls) and extracted twice with ether (150 mls). The aqueous solution is stirred and acidified with concentrated HCl, and the resulting precipitate is filtered off, rinsed well with water, and dried to afford the product (11.7 g): mp=155°-156° C. (dec).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperatureAfter 16 hours the mixture is cooled
  4. customThe residue is partitioned between water (600 mls) and ether (300 mls)
  5. customThe layers are separated
  6. extractionthe aqueous phase extracted twice with ether (200 mls)
  7. washThe combined ether extracts are washed with saturated brine
  8. dry with materialdried over MgSO4
  9. customto leave the crude ester as syrup which also contains mineral oil
  10. temperatureheated
  11. temperatureunder reflux
  12. extractionextracted twice with ether (150 mls)
  13. filtrationthe resulting precipitate is filtered off
  14. washrinsed well with water
  15. customdried

Sources & evidence

ORD record
ord-05f32b9eb043435bbb03a63fced380c7
Source dataset
uspto-grants-1990_03
Patent number
US04910317

Reaction notes

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