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

HRID 2413259Notes

Reaction equation

HRID 2413259 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 dropwise 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-a96ac81a34d94d7f9824d90cac146eb9
Source dataset
uspto-grants-1985_01
Patent number
US04496572

Reaction notes

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