Water → 6-[(6-Methylpyridin-2-yl)oxy]-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63625

Reaction equation

HRID 63625 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.F[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:20][C:16]1[N:15]=[C:14]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 960902-Fluoro-6-methylpyridineHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 1185975886-[(6-Methylpyridin-2-yl)oxy]-1,2,3,4-tetrahydronaphthalen-1-oneYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 6-hydroxy-1-tetralone (3.0 g, 18 mmol), 2-fluoro-6-methylpyridine (2.06 g, 18.5 mmol) and Cs2CO3 (12.1 g, 37.0 mmol) in DMF (150 mL) was stirred at 150° C. in a sealed vessel overnight under N2. The reaction was poured into water (300 mL) and extracted with EtOAc (3×50 mL). Organics were dried (Na2SO4) and concentrated. Purification by silica gel chromatography (PE:EA=5:1) gave 1.2 g (26%) of the title compound as a red oil. [M+H] calc'd for C16H15NO2, 254. found 254.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialOrganics were dried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (PE:EA=5:1)

Sources & evidence

ORD record
ord-c3f01bbcdaaa4bc2b954cfbe82a1dec0
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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