Sodium borohydride → HCID 23080595, compound

HRID 1375965Notes

Reaction equation

HRID 1375965 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:19]=[C:18]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17]3)[C:11]=2[CH3:20])=O)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][C:10]1[C:11]2[C:12]([CH:18]=[CH:17][CH:16]=[CH:15][CH:20]=2)=[C:13]([CH3:14])[CH:19]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69381873HCID 69381873, compound

Product 1

HCID 23080595HCID 23080595, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Boron trifluoride-diethyl ether complex (1.17 ml) was added to a solution of (3-bromophenyl)(1-methylazulen-2-yl) methanone (0.5 g) in diglyme-ether (ratio: 1:1, 2.0 ml) at 0° C. and the mixture was stirred for 20 minutes. Then, sodium borohydride (0.68 g) was added to the reaction mixture and the mixture was stirred at room temperature for one hour. The reaction mixture was added to ice-cooled water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ether) to obtain 1-(3-bromobenzyl)-3-methylazulene (0.21 g).

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. additionThe reaction mixture was added to ice-
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane-ether)

Sources & evidence

ORD record
ord-d6058b214cda4845b8108633cd1f000a
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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