Hydrochloric Acid → Tert-butyl[4-chloro-2-(4-methyl-2-oxopentyl)phenyl]carbamate

HRID 1191644Notes

Reaction equation

HRID 1191644 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=1.[CH:17]([Li])(CC)C.O.Cl.[O:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[C:11]([O:10][C:9](=[O:15])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH2:16][C:28](=[O:24])[CH2:27][CH:26]([CH3:17])[CH3:25])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 14710386tert-Butyl (4-chloro-2-methylphenyl)carbamateHCID 178418400CID 53628100

Product 1

HCID 67684758Tert-butyl[4-chloro-2-(4-methyl-2-oxopentyl)phenyl]carbamate

Procedure

To a solution of tert-butyl (4-chloro-2-methyphenyl)carbamate (483 mg) in tetrahydrofuran (7 mL) was added dropwise sec-butyllithium (1.04 mol/L hexane-cyclohexane solution, 4.3 mL) at −40° C. under an argon atmosphere, and the mixture was stirred for 15 minutes. Then a solution of N-methoxy-N,3-methylbutylamide (319 mg) in tetrahydrofuran (1 mL) was added dropwise, and the mixture was stirred at −40° C. for 15 minutes and at room temperature for 2 hours. Water and 1 mol/L hydrochloric acid were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The aqueous layer was extracted once again with ethyl acetate. The combined organic layers were washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (282 mg).

Workup

  1. stirringthe mixture was stirred at −40° C. for 15 minutes and at room temperature for 2 hours
  2. extractionthis resulting mixture was extracted with ethyl acetate
  3. extractionThe aqueous layer was extracted once again with ethyl acetate
  4. washThe combined organic layers were washed with saturated saline
  5. dry with materialdried over anhydrous magnesium 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-2677bf48b1ee41e2be9868d8c5d79de5
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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