Trifluoroacetic acid → Methyl 4-[(6-methoxy-2-naphthyl)methyl]benzoate

HRID 545452Notes

Reaction equation

HRID 545452 reaction equation
O[CH:2]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=2)[CH:14]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)(Cl)Cl>[CH3:24][O:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH:22]=[CH:21]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67203038Methyl 4-[(RS)-hydroxy(6-methoxy-2-naphthyl)methyl]benzoate

Product 1

HCID 67204017Methyl 4-[(6-methoxy-2-naphthyl)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound of Example 1, Step A (0.97 g, 3 mmol) was treated with 50 mL of chloroform containing 3% each of TFA and triethylsilane for 2 h. The reaction was partitioned between aq sodium bicarbonate and EtOAc. The organic phase was concentrated and the resultant residue was purified by flash chromatography on silica gel (mobile phase=15:85 (v/v) EtOAc:hexanes) to provide the title compound.

Workup

  1. customThe reaction was partitioned between aq sodium bicarbonate and EtOAc
  2. concentrationThe organic phase was concentrated
  3. customthe resultant residue was purified by flash chromatography on silica gel (mobile phase=15:85 (v/v) EtOAc:hexanes)

Sources & evidence

ORD record
ord-e4502f952a3a469f89194e5443668de9
Source dataset
uspto-grants-2011_05
Patent number
US07935713B2

Reaction notes

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