Allyl bromide → 2-Allyl-6-methoxy-tetralin-1-one

HRID 593307Notes

Reaction equation

HRID 593307 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]2.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[CH2:3]([CH:12]1[CH2:11][CH2:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([O:6][CH3:5])[CH:8]=2)[C:13]1=[O:17])[CH:2]=[CH2:1]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 141126-Methoxy-alpha-tetraloneHCID 23665647Potassium tert-butoxide

Product 1

HCID 187945752-Allyl-6-methoxy-tetralin-1-oneYield 20.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl bromide (5.4 g, 45.0 mmol) was added to a solution of 6-methoxy-1-tetralone (10.0 g, 56.0 mmol) and potassium tert-butoxide in THF (50 mL), and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was then diluted with ethyl acetate. The separated organic layer was washed with water, brine solution, dried over sodium sulphate, filtered and removed under reduced pressure. The product was purified by flash chromatography using 4% ethyl acetate in hexanes to afford title compound (2.0 g, 15%) as solid. 1H NMR (400 MHz, CDCl3): δ 8.01 (d, J=8.4 Hz, 1H), 6.80 (dd, J1=2.8 Hz, J2=8.8 Hz, 1H), 6.68 (m, 1H), 5.89-5.79 (m, 1H), 5.12 (t, J=17.2 Hz, 2H) 3.85 (s, 3H), 2.95 (m, 2H), 2.93-2.72 (m, 1H), 2.53-2.46 (m, 1H), 2.29-2.17 (m, 2H), 1.89-1.79 (m, 1H).

Workup

  1. washThe separated organic layer was washed with water, brine solution
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customremoved under reduced pressure
  5. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-bae04a9aa31549ef97b30b276408cab2
Source dataset
uspto-grants-2016_01
Patent number
US09242929B2

Reaction notes

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