Hydrochloric Acid → HCID 67684799, compound

HRID 1191652Notes

Reaction equation

HRID 1191652 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:5]([CH3:17])[CH:4]=1.C([Li])(CC)C.[CH3:23][C:24]([CH3:28])([CH3:27])[CH:25]=[O:26].Cl>O1CCCC1.O>[C:12]([O:11][C:10](=[O:16])[NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:17][CH:25]([OH:26])[C:24]([CH3:28])([CH3:27])[CH3:23])([CH3:13])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12417PivalaldehydeHCID 10609919tert-Butyl (4-methoxy-2-methylphenyl)carbamateHCID 178418400CID 53628100

Product 1

HCID 67684799HCID 67684799, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (4-methoxy-2-methylphenyl)carbamate (475 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 trimethylacetaldehyde (0.287 mL) in tetrahydrofuran (1 mL) was added dropwise, and the mixture was stirred at −40° C. for 15 minutes and at room temperature for additional one hour. Water and μmol/L hydrochloric acid were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and 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 (234 mg).

Workup

  1. stirringthe mixture was stirred at −40° C. for 15 minutes and at room temperature for additional one hour
  2. extractionthis resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-dbaa26ba286a46b4a6060df8fc79e759
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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