Sodium Hydroxide → HCID 66607546, compound

HRID 221129Notes

Reaction equation

HRID 221129 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([CH:8]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][CH:14]=2)O)[CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([CH2:8][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][CH:14]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 66608181HCID 66608181, compound

Product 1

HCID 66607546HCID 66607546, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(2-Pyridyl)thiophene and 5-bromo-2-methylbenzaldehyde obtained in Reference Example 4 were treated in a manner similar to Reference Example 7-(1) to give 5-bromo-2-methylphenyl-5-(2-pyridyl)-2-thienylmethanol as colorless oil. APCI-Mass m/Z 360/362 (M+H). (2) A solution of the above 5-bromo-2-methylphenyl-5-(2-pyridyl)-2-thienylmethanol (1.59 g) in trifluoroacetic acid (40 ml) was cooled to 0° C., and thereto were added gradually sodium triacetoxyborohydride (4.68 g). The mixture was stirred at room temperature for one hour, and cooled again to 0° C. 10% aqueous sodium hydroxide solution was added thereto to basify the reaction mixture. The mixture was extracted with ethyl acetate, and the extract was washed with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired 5-bromo-2-methyl-1-(5-(2-pyridyl)-2-thienylmethyl)benzene (1.38 g) as a colorless solid. APCI-Mass m/Z 344/346 (M+H).

Workup

  1. temperaturecooled again to 0° C
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-6b671934422e485ea127db8c75316f2f
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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