Water → Trifluoro-methanesulfonic acid 5-(3-benzyloxy-phenoxy)-2-formyl-3-methyl-phenyl ester

HRID 1798153Notes

Reaction equation

HRID 1798153 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][C:13]1[CH:20]=[C:19]([CH3:21])[C:16]([CH:17]=[O:18])=[C:15]([OH:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[O:33](S(C(F)(F)F)(=O)=O)[S:34]([C:37]([F:40])([F:39])[F:38])(=O)=[O:35].O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][C:13]1[CH:20]=[C:19]([CH3:21])[C:16]([CH:17]=[O:18])=[C:15]([O:22][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:35])=[O:33])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 866539794-(3-Benzyloxy-phenoxy)-2-hydroxy-6-methyl-benzaldehyde

Product 1

HCID 87325816Trifluoro-methanesulfonic acid 5-(3-benzyloxy-phenoxy)-2-formyl-3-methyl-phenyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-benzyloxy-phenoxy)-2-hydroxy-6-methyl-benzaldehyde (2.5 g, 6.5 mmol) and Et3N (2.72 mL, 19.5 mmol) in DCM (60 mL) at −78° C. was added Tf2O (1.64 mL, 9.76 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 3 hours. Water was added and the solution extracted with DCM (2×25 mL). The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (hexane:EtOAc 80:20) to give trifluoro-methanesulfonic acid 5-(3-benzyloxy-phenoxy)-2-formyl-3-methyl-phenyl ester (2.8 g, 93%). 1H NMR (400 MHz, CDCl3): δ 10.36 (s, 1H), 7.43-7.32 (m, 6H), 6.90 (dd, J=2.0, 8.4 Hz, 1H), 6.79-6.67 (m, 4H), 5.06 (s, 2H), 2.61 (s, 3H). MS (ESI) m/z=467 [M+H]+.

Workup

  1. extractionthe solution extracted with DCM (2×25 mL)
  2. customThe organic extracts were dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel flash column chromatography (hexane:EtOAc 80:20)

Sources & evidence

ORD record
ord-5a63296f1c7f462ea648393f4bf278bd
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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