Water → HCID 21916941, compound

HRID 1978015Notes

Reaction equation

HRID 1978015 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17]C)[CH:15]=2)[CH2:10][CH2:9][CH2:8]1)(=[O:3])[CH3:2].B(Br)(Br)Br.O.C(OCC)(=O)C>ClCCl>[C:1]([NH:4][CH2:5][CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH2:10][CH2:9][CH2:8]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 10422082HCID 10422082, compound

Product 1

HCID 21916941HCID 21916941, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-(acetylamino)ethyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene (3.14 g, 12.7 mmol) in dichloromethane (70 ml) was added dropwise, under ice-cooling, boron tribromide (6.4 g, 25.4 mmol). The reaction mixture was stirred for 50 minutes at room temperature, which was poured into water. The organic layer was subjected to extraction with chloroform. The extract solution was washed with brine and water, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (chloroform:methanol=9:1) to give the above-titled compound (1.54 g, yield 52%), m.p.153-155° C. (recrystallized from ethyl acetate).

Workup

  1. temperaturecooling
  2. extractionThe organic layer was subjected to extraction with chloroform
  3. washThe extract solution was washed with brine and water, which
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (chloroform:methanol=9:1)
  7. customto give

Sources & evidence

ORD record
ord-f4262759f9c145ba894c80956c49d860
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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