Hydrochloric Acid → 2-(2-Chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol

HRID 581733Notes

Reaction equation

HRID 581733 reaction equation
[F:1][C:2]1[C:3]([CH:11]=[O:12])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[Cl:13][CH2:14][CH2:15][O:16][CH2:17][Mg]Cl.[Cl-].[NH4+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:13][CH2:14][CH2:15][O:16][CH2:17][CH:11]([C:3]1[C:2]([F:1])=[CH:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1)[OH:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 15408579Benzo[b]thiophene-5-carboxaldehyde, 6-fluoro-HCID 178478511HCID 178478511, compound

Product 1

HCID 154085802-(2-Chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.6 g of 6-fluorobenzo[b]thiophene-5-carbaldehyde in 30 ml of tetrahydrofuran is dropwise added 10 ml of 1.6 M tetrahydrofuran solution of 2-chloroethoxymethylmagnesium chloride at -30° C. over ten minutes, and thereafter, the resulting mixture is stirred while ice-cooling for one hour. Subsequently, the thus stirred reaction mixture is introduced into a mixture of 50 ml of ice water, 50 ml of ethyl acetate and 2 g of ammonium chloride, and the resulting mixture is adjusted to pH 2 with 6 N hydrochloric acid. Thereafter, the thus pH-adjusted mixture is stirred at the same temperature for five minutes. Subsequently, the thus stirred reaction mixture is adjusted to pH 6 with a saturated aqueous sodium hydrogencarbonate solution. Thereafter, the resulting organic layer is separated, washed successively with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The solvent is then removed from the thus dried layer by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluent:toluene:ethyl acetate=4:1], to obtain 1.3 g of oily 2-(2-chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol.

Workup

  1. customat -30° C.
  2. customover ten minutes
  3. temperaturecooling for one hour
  4. customSubsequently, the thus stirred reaction mixture
  5. stirringThereafter, the thus pH-adjusted mixture is stirred at the same temperature for five minutes
  6. customSubsequently, the thus stirred reaction mixture
  7. customThereafter, the resulting organic layer is separated
  8. washwashed successively with water
  9. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  10. customThe solvent is then removed from the thus dried layer by distillation under reduced pressure
  11. customThe residue obtained
  12. customis purified by a column chromatography [eluent:toluene:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-55e7be8f4b294678ae929bc850897979
Source dataset
uspto-grants-1999_07
Patent number
US05922721

Reaction notes

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