1-[(2-methylpropan-2-yl)oxy]propan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.5 g of 3-chloro-4-hydroxybenzoic acid methyl ester in 20 ml of THF, 1.8 ml of 1-tert-butoxy-2-propanol, 3.16 g of triphenylphosphine, and 1.9 ml of diethylazodicarboxylate were added, and the mixture was stirred at room temperature for 1 hour. After evaporation of the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=100:1˜5:1) to obtain 2.3 g of 4-(1-tert-butoxy-2-propoxy)-3-chlorobenzoic acid methyl ester. After evaporation of the solvent under reduced pressure the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=100:1˜5:1)

Conditions: temp:37.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-tert-butoxypropan-2-ol (293 μl, 1937 μmol) in DMF (2.5 mL) under nitrogen was added NaH (93 mg, 3873 μmol) at 23° C. After 10 min, 4-chloro-7-methoxyquinoline (250 mg, 1291 μmol) was added. The mixture was heated to 37° C. for 18 h. The reaction was partioned between 5% NaHCO3 (10 mL) and CH2Cl2 (15%). The aqueous was extracted with CH2Cl2 (10 mL). The combined organics were dried with brine and MgSO4, concentrated under reduced pressure from toluene, and purified on silica (12 g) eluting with 0-30% of 5% (MeOH/CH2Cl2). MS (ESI pos. ion) m/z (MH+): 290. Calc'd exact mass for C17H23NO3: 291. 1H NMR (400 MHz, Chloroform-d) δ ppm 1.19 (s, 9H) 1.44 (d, J=6.26 Hz, 3H) 3.46-3.54 (m, 2H) 3.69 (dd, J=9.49, 5.77 Hz, 1H) 3.93 (s, 3H) 4.69-4.77 (m, 1H) 6.70 (d, J=5.28 Hz, 1H) 7.12 (dd, J=9.19, 2.54 Hz, 1H) 7.34 (d, J=2.54 Hz, 1H) 8.10 (d, J=9.19 Hz, 1H) 8.63 (d, J=5.48 Hz, 1H). 13C NMR (101 MHz, Chloroform-d) δ ppm 17.15, 27.45, 50.29, 55.40, 65.09, 73.31, 74.06, 100.45, 106.89, 116.62, 118.04, 123.38, 151.26, 151.58, 160.89, 161.07 The aqueous was extracted with CH2Cl2 (10 mL) The combined organics were dried with brine and MgSO4 concentrated under reduced pressure from toluene purified on silica (12 g) eluting with 0-30% of 5% (MeOH/CH2Cl2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.5 g of 3-chloro-4-hydroxybenzoic acid methyl ester in 20 ml of THF, 1.8 ml of 1-tert-butoxy-2-propanol, 3.16 g of triphenylphosphine, and 1.9 ml of diethylazodicarboxylate were added, and the mixture was stirred at room temperature for 1 hour. After evaporation of the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=100:1˜5:1) to obtain 2.3 g of 4-(1-tert-butoxy-2-propoxy)-3-chlorobenzoic acid methyl ester. After evaporation of the solvent under reduced pressure the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=100:1˜5:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.5 g of 3-chloro-4-hydroxybenzoic acid methyl ester in 20 ml of THF, 1.8 ml of 1-tert-butoxy-2-propanol, 3.16 g of triphenylphosphine, and 1.9 ml of diethylazodicarboxylate were added, and the mixture was stirred, at room temperature for 1 hour. After evaporation of the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=100:1˜5:1) to obtain 2.3 g of 4-(1-tert-butoxy-2-propoxy)-3-chlorobenzoic acid methyl ester. After evaporation of the solvent under reduced pressure the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=100:1˜5:1)