Bis(2-bromoethyl) ether → HCID 66833987, compound

HRID 61816

Reaction equation

HRID 61816 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br.[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[C:10]32[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 777857-Methoxy-2-tetralone2×

Product 1

HCID 66833987HCID 66833987, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the THF (300 ml) solution of 7-methoxy-3,4-dihydro-1H-naphthalen-2-one (Compound A1, 20 g, 0.11 mol), sodium hydride (9.9 g, 3.7 eq.) was added at 0° C. After stirring for 10 min, 1-bromo-2-(2-bromo-ethoxy)-ethane (19 ml, 12 eq.) was added dropwise thereto, and the mixture was stirred at 80° C. for 3 hr. To the reaction solution, saturated aqueous solution of ammonium chloride was added and the extraction was carried out twice with ethyl acetate. The organic layer was dried over magnesium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (white solid, 13 g, 51%).

Workup

  1. stirringthe mixture was stirred at 80° C. for 3 hr
  2. extractionthe extraction
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-36c2b552965943daa97eb9dbe64a655a
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Linked notes

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