Ethyl Acetate → HCID 86626747, compound

HRID 603986Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])[CH3:15].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:14]([N:16]([CH2:17][CH2:18][O:19][CH3:20])[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:15]

Participants

Conditions

Temperature: 120 °C

Procedure

2-Fluoro-5-trifluoromethyl-benzaldehyde (2.7 g) and ethyl-(2-methoxy-ethyl)-amine (2.18 g) are dissolved in toluene (20 ml), and thereto is added potassium carbonate (5.83 g) and the mixture is stirred at 120° C. overnight. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and a saturated brine and the mixture is separated, and the organic layer is washed with a saturated brine, and the mixture is dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give 2-[ethyl-(2-methoxy-ethyl)-amino]-5-trifluoromethyl-benzaldehyde (3.75 g). MS (m/z): 276 [M+H]+

Workup

temperatureThe reaction solution is cooled to room temperature
customa saturated brine and the mixture is separated
washthe organic layer is washed with a saturated brine
dry with materialthe mixture is dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

Sources & evidence

ORD record: ord-36b1c91ed77a46418c9b9dcd92737991
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906517B2

Reaction notes

Loading…