Dimethylformamide → 5-(Benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 131645Notes

Reaction equation

HRID 131645 reaction equation
C(O[K])(C)(C)C.CN(C)C=O.[OH:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][C:18]2=[O:23].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][C:18]2=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 1199215-Hydroxy-1-tetraloneHCID 178418922HCID 178418922, compound

Product 1

HCID 105869155-(Benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.1 g of t-butoxypotassium was added under ice cooling and nitrogen replacement to a 50 mL dimethylformamide solution of 4.0 g of 5-hydroxytetralone, and the system was stirred for 15 minutes at the same temperature, after which 3.2 mL of benzyl bromide was added, and the system was stirred for 2 hours at the same temperature. After the reaction, water was added, extraction was performed with ethyl acetate, and the organic layer was washed with saturated brine and dried with magnesium sulfate, then subjected to reduced-pressure solvent distillation, and the residue was refined by silica gel column chromatography (20% ethyl acetate/hexane) to obtain 6.3 g of 5-benzyloxytetralone (compound 2-7 in Table 3-1) in the form of a colorless solid.

Workup

  1. additionwas added
  2. extractionextraction
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. distillationsubjected to reduced-pressure solvent distillation

Sources & evidence

ORD record
ord-9f1f1b83711341b69f8cd650bf3ddf8d
Source dataset
uspto-grants-2008_06
Patent number
US07384974B2

Reaction notes

Loading…