Hydrochloric Acid → HCID 69516717, compound

HRID 855071Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH:12]([CH3:14])[CH3:13])=[C:4]([C:7]([OH:11])=[C:8]([CH3:10])[CH:9]=1)[CH:5]=O.C([O-])([O-])=O.[K+].[K+].[F:21][C:22]([F:31])([F:30])/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26].Cl>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH:12]([CH3:14])[CH3:13])=[C:4]2[C:7](=[C:8]([CH3:10])[CH:9]=1)[O:11][CH:23]([C:22]([F:21])([F:31])[F:30])[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:5]2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-chloro-6-hydroxy-2-isopropyl-5-methylbenzaldehyde (1.83 g, 8.6 mmole), K2CO3 (2.38 g, 17.3 mmole) and ethyl 4,4,4-trifluorocrotonate (2.17 g, 12.9 mmole) in anhydrous DMF (10.0 mL) was heated to 90° C. under a dry N2 atmosphere for 18 hrs. The mixture was then cooled, poured into 0.5 N HCl (50 ml) and extracted with EtOAc (2×50 mL). The combined extracts were washed with brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo to give a dark oil which was subject to flash chromatography (silica gel) and eluted with 50% CH2Cl2/hexanes to give a yellow oil (2.1 g, 68%): GCMS m/z 362.0 (M+). 1H NMR (CDCl3/400 MHz) 8.07 (s, 1H), 7.02 (s, 1H), 5.64 (q, 1H, J=7.0 Hz), 4.23 (m, 2H), 3.39 (s, 3H), 3.23 (m, 1H), 1.26 (m, 3H), 1.12 (m, 6H).

Workup

temperatureThe mixture was then cooled
extractionextracted with EtOAc (2×50 mL)
washThe combined extracts were washed with brine (50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a dark oil which
washeluted with 50% CH2Cl2/hexanes

Sources & evidence

ORD record: ord-15509c452ae745bdb039af06c3e56f9f
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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