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

HRID 1798061Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:7]=[C:6]([CH2:17][O:18][CH3:19])[C:3]=1[CH:4]=[O:5].CCN(CC)CC.[O:27](S(C(F)(F)F)(=O)=O)[S:28]([C:31]([F:34])([F:33])[F:32])(=O)=[O:29]>ClCCl.O>[CH:4]([C:3]1[C:6]([CH2:17][O:18][CH3:19])=[CH:7][C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:9][C:2]=1[O:1][S:28]([C:31]([F:34])([F:33])[F:32])(=[O:29])=[O:27])=[O:5]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (3.09 g, 11.62 mmol) and Et3N (6.47 mL, 46.48 mmol) in dichloromethane (50 mL) was added Tf2O (4.30 mL, 25.56 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 2-formyl-3-methoxymethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl ester (2.60 g, 72%). 1H NMR (400 MHz, CDCl3) δ 10.30 (s, 1H), 7.44 (s, 1H), 7.00 (s, 1H), 5.60 (s, 1H), 4.80 (s, 2H), 3.80 (m, 1H), 3.65 (m, 1H), 3.50 (s, 3H), 2.00-1.50 (m, 6H).

Workup

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-53b0e2446a5d4f09aa4bf9c5de358b26
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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