Dimethyl Sulfoxide → 6-(2,6-Diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehyde

HRID 251602Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH3:20])[C:14]=1[C:21]1[N:26]=[CH:25][C:24]([CH2:27][OH:28])=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=1)[CH3:12]>C(Cl)Cl.C1COCC1.CCOCC>[CH2:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH3:20])[C:14]=1[C:21]1[N:26]=[CH:25][C:24]([CH:27]=[O:28])=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=1)[CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of dry DMSO (2.5 g, 32 mmol) in CH2Cl2 (2 mL) is added dropwise to a solution of oxalyl chloride (2M in CH2Cl2, 7.5 mL) in CH2Cl2 (80 mL) at −78° C. After 10 minutes, a solution of [6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol (3.4 g, 11.4 mmol) in THF (20 mL) is added to the above mixture. Fifteen minutes after addition, TEA (10 mL) is added and the mixture is stirred at −78° C. for 15 minutes and then warmed to room temperature. The mixture is diluted with ether (100 mL) and washed with water (2×50 mL). The organic layer is dried and concentrated. The crude product is purified on a silica gel:column (4:1 Hexane/EtOAc) to give 6-(2,6-diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehyde. 1H NMR (CDCl3) 10.53 (s, 1H), 8.98 (s, 1H), 7.30 (t, 1H), 7.15 (d, 2H), 6.89 (s, 1H), 4.20 (q, 2H), 2.34 (m, 4H), 1.54 (t, 3H), 1.06 (t, 9H).

Workup

additionis added
temperaturewarmed to room temperature
washwashed with water (2×50 mL)
customThe organic layer is dried
concentrationconcentrated
customThe crude product is purified on a silica gel

Sources & evidence

ORD record: ord-09f8f85b43a648ae9f3b87c630ad895c
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863454B2

Reaction notes

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