Ammonium Chloride → 7-Bromo-1-hydroxy-1-methyl-2-(3-pyridylmethyl)-1,2,3,4-tetrahydronaphthalene

HRID 280622Notes

Reaction equation

HRID 280622 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]([CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[C:12]2=[O:15])=[CH:7][CH:6]=1.[Cl-].[NH4+]>CCOCC.O1CCCC1>[Br:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]([CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[C:12]2([OH:15])[CH3:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 233208987-Bromo-2-(3-pyridylmethyl)-1-tetraloneHCID 178418573HCID 178418573, compound

Product 1

HCID 233209037-Bromo-1-hydroxy-1-methyl-2-(3-pyridylmethyl)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium bromide (15 ml of a 3M solution in ether) was added dropwilse over 5 minutes to a stirred solution of 7-bromo-2-(3-pyridylmethyl)-1-tetralone (3.20 g) in dry tetrahydrofuran (50 ml). The resulting mixture was heated under reflux with stirring for 10 hours and then cooled. An excess of aqueous ammonium chloride solution was added and the mixture was extracted several times with ether. The combined ethereal extracts were dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel. Elution with chloroform gave 7-bromo-1-hydroxy-1-methyl-2-(3-pyridylmethyl)-1,2,3,4-tetrahydronaphthalene (2.87 g) as a mixture of isomers which was used directly in the next stage.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. extractionthe mixture was extracted several times with ether
  5. dry with materialThe combined ethereal extracts were dried (Na2SO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washElution with chloroform

Sources & evidence

ORD record
ord-07a54fbf39cf4734bd387887bf7a4251
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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