Triethylamine → Trifluoro-methanesulfonic acid 3-ethyl-2-formyl-5-(tetrahydro-pyran-2-yloxy)-phenyl ester

HRID 1798028Notes

Reaction equation

[CH2:1]([C:3]1[CH:10]=[C:9]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:8]=[C:7]([OH:18])[C:4]=1[CH:5]=[O:6])[CH3:2].CCN(CC)CC.[O:26](S(C(F)(F)F)(=O)=O)[S:27]([C:30]([F:33])([F:32])[F:31])(=O)=[O:28]>ClCCl.O>[CH2:1]([C:3]1[C:4]([CH:5]=[O:6])=[C:7]([O:18][S:27]([C:30]([F:33])([F:32])[F:31])(=[O:28])=[O:26])[CH:8]=[C:9]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:10]=1)[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-ethyl-6-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (1.56 g, 6.24 mmol) and Et3N (2.61 mL, 18.72 mmol) in dichloromethane (20 mL) was slowly added Tf2O (2.10 mL, 12.84 mmol) at −78° C. The mixture was stirred at −78° C. for 1 hour. The mixture was diluted with H2O and extracted with dichloromethane. The organic extracts were washed with brine, dried and concentrated in vacuo. The residue was dissolved in Hexane-EtOAc(4:1), filtered through a plug of silica gel and filtrate was concentrated to give trifluoro-methanesulfonic acid 3-ethyl-2-formyl-5-(tetrahydro-pyran-2-yloxy)-phenyl ester (2.06 g, quant.). 1H NMR (400 MHz, CDCl3δ 12.39 (s, 1H), 10.08 (s, 1H), 6.98 (s, 1H), 6.90 (s, 1H), 5.50 (s, 1H), 3.80 (m, 1H), 3.66 (m, 1H), 3.07 (m, 2H), 2.00-1.50 (m, 6H), 1.26 (m, 3H).

Workup

customat −78° C
extractionextracted with dichloromethane
washThe organic extracts were washed with brine
customdried
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in Hexane-EtOAc(4:1)
filtrationfiltered through a plug of silica gel and filtrate
concentrationwas concentrated

Sources & evidence

ORD record: ord-aa33f262a8b84d23bdce8a5d2da928c7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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