Hydrochloric Acid → HCID 69517429, compound

HRID 855061Notes

Reaction equation

[CH:1]([C:3]1[C:4]([OH:15])=[C:5]([CH:11]=[C:12]([CH3:14])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.C([O-])([O-])=O.[K+].[K+].C(N(CC)CC)C.[F:29][C:30]([F:39])([F:38])/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34].Cl>CS(C)=O>[CH3:14][C:12]1[CH:13]=[C:3]2[C:4](=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:11]=1)[O:15][CH:31]([C:30]([F:29])([F:39])[F:38])[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:1]2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 3-formyl-2-hydroxy-5-methylbenzoate (6.18 g, 29.69 mmole), K2CO3 (8.19 g, 59.38 mmole), triethylamine (1.99 g, 118.75 mmole), and ethyl 4,4,4-trifluorocrotonate (19.95 g, 118.75 mmole) in anhydrous DMSO (40.0 mL) was heated to 90° C. under a dry N2 atmosphere for 5 hrs. The mixture was then cooled and allowed to stir at room temperature for 15 hours. The reaction was poured into 1.2 N HCl (100 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give a dark red oil which was subject to flash chromatography (silica gel) and eluted with 100% CH2Cl2 to give a light orange solid (4.5 g, 42%): 1H NMR (acetone-d6/400 MHz) 7.84 (s, 1H), 7.61 (s, 1H), 7.46 (s, 1H), 5.86 (q, 1H, J=7.0 Hz), 4.30 (m, 4H), 2.31 (s, 3H), 1.33 (m, 6H).

Workup

temperatureThe mixture was then cooled
extractionextracted with EtOAc (2×100 mL)
washThe combined extracts were washed with brine (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a dark red oil which
washeluted with 100% CH2Cl2

Sources & evidence

ORD record: ord-891780fd19fb413ca174b985f9e3b0bd
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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