Trifluoroacetic acid → HCID 11694142, compound

HRID 643577Notes

Reaction equation

HRID 643577 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:11]=[C:8]([CH:9]=O)[C:7]([OH:12])=[CH:6][CH:5]=1.C(=O)(OC(C)(C)C)[NH2:16].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[NH2:16][CH2:9][C:8]1[CH:11]=[C:4]([O:3][C:2]([F:14])([F:13])[F:1])[CH:5]=[CH:6][C:7]=1[OH:12]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 77922tert-Butyl carbamateHCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehyde

Product 1

HCID 11694142HCID 11694142, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(trifluoromethoxy)salicylaldehyde (4.85 mmol, 1.0 g), tert-butyl carbamate (14.55 mmol, 1.70 g), triethylsilane (14.55 mmol, 2.3 mL), trifluoroacetic acid (9.7 mmol, 0.72 mL) in acetonitrile was stirred at room temperature overnight. The reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and purified by silica gel chromatography (15%-100% EtOAc/hexane). The resulting yellow solid was then dissolved in a mixture of TFA (10 mL) and dichloromethane (20 mL) and stirred for 2 hours at room temperature. The volatile solvents were then removed by rotovap to afford 2-(aminomethyl)-4-(trifluoromethoxy)phenol as a yellow oil. 1H NMR (CD3OD) 7.28 (s, 1H), 7.22 (m, 1H), 6.97 (m, 1H), 4.13 (s, 2H), 1.59 (s, 1H).

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. custompurified by silica gel chromatography (15%-100% EtOAc/hexane)
  5. dissolutionThe resulting yellow solid was then dissolved in a mixture of TFA (10 mL) and dichloromethane (20 mL)
  6. customThe volatile solvents were then removed by rotovap

Sources & evidence

ORD record
ord-8455746be98448b09a0da6c48299ad3d
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

Loading…