Hydrochloric Acid → HCID 15599371, compound

HRID 867464Notes

Reaction equation

HRID 867464 reaction equation
C([O:4][C:5]1[C:6]([CH:14]=[CH:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[CH:7][C:8]2[O:12][CH2:11][CH2:10][C:9]=2[CH:13]=1)(=O)C.Cl>C(O)C.[Pd]>[OH:4][C:5]1[C:6]([CH2:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[CH:7][C:8]2[O:12][CH2:11][CH2:10][C:9]=2[CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53781331HCID 53781331, compound

Product 1

HCID 15599371HCID 15599371, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(5-acetoxy-2,3-dihydrobenzofuran-6-yl)-2-(2-thienyl)ethene (0.55 g, 0.0019 mol), in ethanol (20 ml) and 12N HCl (0.5 ml) was hydrogenated at 40 psi using 10% Pd/C (0.55 g) as catalyst. After filtration and concentration the crude 5-acetoxy-6-(2-(2-thienyl)ethyl)-2,3-dihydrobenzofuran was dissolved in methylene chloride (20 ml) and washed with saturated sodium bicarbonate (2×10 ml) saturated sodium chloride (10 ml) and concentrated. The resulting yellow oil was dissolved in ethanol (10 ml) and 50% NaOH (0.2 ml). The mixture was allowed to stir for 1/2 hour at room temperature and was concentrated. The crude product was dissolved in methylene chloride (20 ml) and washed with 10% acetic acid (10 ml), saturated sodium carbonate (10 ml), saturated sodium chloride (10 ml). The combined organic layers were dried (MgSO4), and concentrated to a dark oil. Purification by chromatography over silica gel (hexane/ethyl acetate, 90/10, as eluent) afforded 5-hydroxy-6-(2-(2-thienyl)ethyl)-2,3-dihydrobenzofuran (66 mg, 13%). m.p. 79°-85° C.

Workup

  1. filtrationAfter filtration and concentration the crude 5-acetoxy-6-(2-(2-thienyl)ethyl)-2,3-dihydrobenzofuran
  2. dissolutionwas dissolved in methylene chloride (20 ml)
  3. washwashed with saturated sodium bicarbonate (2×10 ml) saturated sodium chloride (10 ml)
  4. concentrationconcentrated
  5. dissolutionThe resulting yellow oil was dissolved in ethanol (10 ml)
  6. concentrationwas concentrated
  7. dissolutionThe crude product was dissolved in methylene chloride (20 ml)
  8. washwashed with 10% acetic acid (10 ml), saturated sodium carbonate (10 ml), saturated sodium chloride (10 ml)
  9. dry with materialThe combined organic layers were dried (MgSO4)
  10. concentrationconcentrated to a dark oil
  11. customPurification by chromatography over silica gel (hexane/ethyl acetate, 90/10, as eluent)

Sources & evidence

ORD record
ord-24bfeee32a6e480b92eadd1998683b9a
Source dataset
uspto-grants-1988_10
Patent number
US04775679

Reaction notes

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