Potassium Carbonate → 5-(Cyclopropylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63079Notes

Reaction equation

HRID 63079 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].Br[CH2:14][CH:15]1[CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC.CCOC(C)=O>[CH:15]1([CH2:14][O:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH2:4][CH2:5][CH2:6][C:7]3=[O:12])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 1199215-Hydroxy-1-tetralone

Product 1

HCID 654540615-(Cyclopropylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-oneYield 79.9%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-hydroxy-1-tetralone (1.8 g, 11.0 mmol) in butanone was added (bromomethyl)cyclopropane (1.8 g, 13.2 mmol) and K2CO3 (3.0 g, 22.0 mmol) at rt. The mixture was heated at 80° C. overnight. After the reaction was cooled to rt, it was diluted with EtOAc, filtered, and concentrated. The residue was purified by silica gel chromatography (20:1 PE/EtOAc) to give 1.9 g (78%) of the title compound as a tan oil. 1H NMR (300 MHz, CDCl3): δ 0.35-0.40 (2H, m), 0.62-0.68 (2H, m), 1.27-1.32 (1H, m), 2.05-2.17 (2H, m), 2.64 (2H, t, J=6.6 Hz), 2.96 (2H, t, J=6.0 Hz), 3.86 (2H, d, J=6.9 Hz), 6.98 (1H, d, J=8.1 Hz), 7.24 (1H, t, J=8.7 Hz), 7.65 (1H, d, J=8.1 Hz).

Workup

  1. temperatureAfter the reaction was cooled to rt
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (20:1 PE/EtOAc)

Sources & evidence

ORD record
ord-88896bce4ac5456a97494cb321ae2e99
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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