Hydrochloric Acid → HCID 178521618, compound

HRID 254415Notes

Reaction equation

HRID 254415 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][C:10](=[O:12])[CH2:9]2)=[CH:4][CH:3]=1.O.[Cl-].[NH4+].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:9][C@H:10]([OH:12])[CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 45896953-(4-Bromophenyl)cyclobutan-1-oneHCID 57429219Ammonium chloride monohydrate

Product 1

HCID 178521618HCID 178521618, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −78° C., 1.0 M tri(tert-butoxy)lithiumaluminium hydride (24 mL, 24 mmol) was added to a THF (20 mL) solution of 3-(4-bromophenyl)cyclobutanone (4.53 g, 20.1 mmol), and stirred at the same temperature for 1.5 hours. Saturated ammonium chloride water and 1 N hydrochloric acid were added to the reaction liquid, extracted with ethyl acetate, dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, the obtained residue was purified by silica gel column chromatography (C-200, ethyl acetate:hexane=1:4 to 3:7) to obtain the entitled compound (3.04 g, 66%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried with anhydrous magnesium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (C-200, ethyl acetate:hexane=1:4 to 3:7)

Sources & evidence

ORD record
ord-ffd1d72c1d7a4c14a619a620f99ba6ee
Source dataset
uspto-grants-2011_01
Patent number
US07875633B2

Reaction notes

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