Water → HCID 131731723, compound

HRID 2400285Notes

Reaction equation

HRID 2400285 reaction equation
[Cl:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]([CH3:16])=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.[CH:19]([Li])(CC)C.[Cl-].[NH4+].O.[O:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[C:11]([O:10][C:9](=[O:15])[NH:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([O:17][CH3:18])=[CH:4][C:5]=1[CH2:16][CH:31]([OH:27])[CH:30]([CH3:19])[CH2:29][CH3:28])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 69097022HCID 69097022, compoundHCID 178418400CID 53628100

Product 1

HCID 131731723HCID 131731723, compound

Procedure

Under an argon atmosphere, to a solution of tert-butyl (5-chloro-4-methoxy-2-methylphenyl)carbamate (1.00 g) in tetrahydrofuran (18.4 mL) was added dropwise sec-butyllithium (1.08 mol/L hexane-cyclohexane solution, 7.5 mL) at −45° C., and the mixture was stirred for 30 minutes. Next, a solution of 2-methylbutyl aldehyde (0.430 mL) in tetrahydrofuran (1.84 mL) was added dropwise thereto, and the mixture was stirred at −45° C. for 35 minutes and then stirred at room temperature for 90 more minutes. To the reaction mixture was added saturated aqueous ammonium chloride solution/water (3/1, 40 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (876 mg). 1H-NMR (CDCl3) δ ppm: 0.50-2.30 (19H, m), 2.45-2.95 (2H, m), 3.55-4.05 (4H, m), 6.60-6.80 (1H, m), 7.20-8.00 (2H, m).

Workup

  1. stirringthe mixture was stirred at −45° C. for 35 minutes
  2. stirringstirred at room temperature for 90 more minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer 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 (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d0fa1edd451c4847982b68de7917f633
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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