Anisole → HCID 69334713, compound

HRID 350555Notes

Reaction equation

HRID 350555 reaction equation
C(OC([NH:8][CH2:9][C:10]([CH3:23])([O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)[CH3:11])=O)(C)(C)C.C1(OC)C=CC=CC=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:8][CH2:9][C:10]([CH3:23])([O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)[CH3:11]

Participants

5

Reactant 2

HCID 7519AnisoleHCID 69334030HCID 69334030, compound

Product 1

HCID 69334713HCID 69334713, compoundYield 116.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of methyl 4-(1-tert-butoxycarbonylamino-2-methyl-2-propoxy)benzoate (460 mg, 1.42 mmol) and anisole (0.155 mL, 1.42 mmol) in CH2Cl2(15 mL) and TFA (3 mL) was stirred for 3 hr at room temp. The mixture was evaporated off. The residue was dissolved in CH2Cl2 (30 mL) and made basic by the addition of 0.5 N NaOH. The CH2Cl2 layer was separated, dried over Na2SO4, and evaporated. The residue was chromatographed on silica-gel with CH2Cl2 as eluent to give 370 mg (100%) methyl 4-(1-amino-2-methyl-2-propoxy)benzoate as a gum. 1H-NMR (CDCl3) δ 1.34 (s, 6H), 2.87 (s, 2H), 3.90 (s, 3H), 7.10 (d, J=8.8 Hz, 2H), 7.97 (d, J=8.8 Hz, 2H).

Workup

  1. customThe mixture was evaporated off
  2. dissolutionThe residue was dissolved in CH2Cl2 (30 mL)
  3. additionmade basic by the addition of 0.5 N NaOH
  4. customThe CH2Cl2 layer was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was chromatographed on silica-gel with CH2Cl2 as eluent

Sources & evidence

ORD record
ord-89a9c8992b1847a8937d5a50fe8ad62b
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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