Benzaldehyde → HCID 86644410, compound

HRID 2194676Notes

Reaction equation

HRID 2194676 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1>[OH:30][CH:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[S:6][C:5]([CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 25517Ammonium ChlorideHCID 86644409HCID 86644409, compound

Product 1

HCID 86644410HCID 86644410, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl [(5-bromo-4-phenyl-2-thienyl)methyl]methylcarbamate (1.0 g) in tetrahydrofuran was cooled to −78° C., and 1.6 mol/L n-butyllithium-hexane solution (1.96 mL) was added dropwise. After stirring at the same temperature for 1 hr, benzaldehyde (334 mg) in tetrahydrofuran (3 mL) was added dropwise. The mixture was gradually warmed to room temperature, and stirred for 2 hr. The reaction mixture was treated with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→9:1) to give the title compound as a pale-yellow oil (yield 607 mg, yield 57%).

Workup

  1. addition1.6 mol/L n-butyllithium-hexane solution (1.96 mL) was added dropwise
  2. stirringstirred for 2 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→9:1)

Sources & evidence

ORD record
ord-03537d212cc54d6eb624463605da6064
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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