Sulfuric Acid → HCID 86717831, compound

HRID 591016Notes

Reaction equation

HRID 591016 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Br:11][C:12]1[C:16]2=[C:17]3[C:22](=[CH:23][CH:24]=[C:15]2[S:14][C:13]=1[C:25](OCC)=[O:26])[N:21]=[CH:20][CH:19]=[CH:18]3.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Br:11][C:12]1[C:16]2=[C:17]3[C:22](=[CH:23][CH:24]=[C:15]2[S:14][C:13]=1[CH2:25][OH:26])[N:21]=[CH:20][CH:19]=[CH:18]3

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 21225700DiisobutylaluminumhydrideHCID 86717832HCID 86717832, compound

Product 1

HCID 86717831HCID 86717831, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under nitrogen atmosphere at −10° C., a solution of diisobutylaluminium hydride 1M in toluene (2.34 mL, 2.34 mmol) was added slowly to a solution of ethyl 1-bromothieno[3,2-f]quinoline-2-carboxylate (16d) in toluene (17 mL). Then the mixture was stirred at room temperature for 20 minutes more. The mixture was cooled in an ice bath and a solution of sulfuric acid 5% (5 mL) was added. The mixture was basified with saturated aqueous sodium hydrogencarbonate and extracted twice with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate and evaporated under reduced pressure to give the desired alcohol (16e) as a yellow powder (200 mg, 0.68 mmol, 87%).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7d8e292d6aa941d39947882b70e8e91a
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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