Hydrochloric Acid → HCID 13552981, compound

HRID 745532Notes

Reaction equation

HRID 745532 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:11][C:12]1[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=1[CH:14](O)[C:15]1[CH:19]=[CH:18]S[CH:16]=1.S(=O)(=O)(O)[OH:26].Cl>C(OCC)C>[O:26]1[CH:18]=[CH:19][C:15]([CH2:14][C:13]2[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=2[Br:11])=[CH:16]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 23313702HCID 23313702, compound

Product 1

HCID 13552981HCID 13552981, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

Aluminum chloride (78.0 mmol) dissolved in diethyl ether (40 mL) under nitrogen was added to a suspension of lithium aluminum hydride (78.0 mmol) in diethyl ether (40 mL) under nitrogen at 0° C. To the reaction mixture was added a solution of Compound 3a (52.0 mmol) in diethyl ether (25 mL) at such a rate that reflux was maintained. After an additional 15 minutes at reflux, the reaction mixture was cooled to 0° C. and dilute 3M sulfuric acid was added dropwise until the evolution of gas stopped. The reaction mixture was then poured onto ice (100 mL) and 3N hydrochloric acid (25 mL) and then extracted with diethyl ether (2×50 mL). The combined organic phases were washed with 3N hydrochloric acid, saturated aqueous sodium bicarbonate, water and brine and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel eluted with ethyl acetate:hexane (2:98) to afford Compound 3b as an oil (Rf =0.4).

Workup

  1. temperaturethat reflux
  2. temperaturewas maintained
  3. temperatureAfter an additional 15 minutes at reflux
  4. additionwas added dropwise until the evolution of gas
  5. extractionextracted with diethyl ether (2×50 mL)
  6. washThe combined organic phases were washed with 3N hydrochloric acid, saturated aqueous sodium bicarbonate, water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe residue purified by flash chromatography on silica gel
  10. washeluted with ethyl acetate:hexane (2:98)

Sources & evidence

ORD record
ord-9a24bc7f13fb4ee6b4c951df93c2400a
Source dataset
uspto-grants-1986_07
Patent number
US04599341

Reaction notes

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