Hydrochloric Acid → 6-Methoxybenzo[b]thiophene-2-ethanol

HRID 1835692Notes

Reaction equation

HRID 1835692 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[CH:14][S:13][C:12]=2[CH:16]=1.[CH2:17]1[O:19][CH2:18]1.Cl>O1CCCC1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[C:14]([CH2:17][CH2:18][OH:19])[S:13][C:12]=2[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 136342376-Methoxy-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 235006406-Methoxybenzo[b]thiophene-2-ethanolYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

Butyllithium (2.5 M) (0.27 mol) was added dropwise to 6-methoxybenzo[b]-thiophene (0.25 mol) in tetrahydrofuran (1000 ml), stirred at −30° C. The mixture was stirred for 10 min at −30° C. Ethylene oxide (0.38 mol in 100 ml tetrahydrofuran) was added dropwise at −30° C. The mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was acidified with dilute HCl solution. The solvent was evaporated. The residue was diluted with water and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was stirred in hexane, filtered off and dried, yielding 41.3 g of 6-methoxybenzo[b]thiophene-2-ethanol (interm. 3).

Workup

  1. stirringThe mixture was stirred for 10 min at −30° C
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 hours
  4. customThe solvent was evaporated
  5. additionThe residue was diluted with water
  6. extractionthis mixture was extracted with CH2Cl2
  7. customThe separated organic layer was dried
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. stirringThe residue was stirred in hexane
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-586c639cedb14bb08651ea24f6e8c57f
Source dataset
uspto-grants-2004_08
Patent number
US06774129B2

Reaction notes

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