Triethylamine → HCID 89462556, compound
Reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][PH:11](=[O:15])[O:12][CH2:13][CH3:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([P:11]([CH3:10])(=[O:15])[O:12][CH2:13][CH3:14])=[CH:3][CH:4]=1)=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 4-bromobenzaldehyde, 38-a, (500 mg, 2.7 mmol) and ethyl methylphosphinate, 38-b, (650 mg, 5.4 mmol) in toluene (10 mL) was added triethylamine (1.1 g, 11 mmol). After being allowed to stir for 10 h at 110° C. under nitrogen atmosphere, the mixture was cooled to ambient temperature, concentrated, diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (2×30 mL), dried over Na2SO4, filtrated and concentrated to give a residue, which was purified by chromatography on silica gel (dichloromethane/methanol=70:1) to afford compound 38-c as a colorless oil. (530 mg, 93%). 1H NMR (300 MHz, DMSO-d6) δ 10.08 (s, 1H), 7.93-8.05 (m, 4H), 3.90-3.98 (m, 2H), 1.68-1.73 (d, J=14.4 Hz, 3H), 1.16-1.24 (m, 3H). LC-MS 213 [M+H]+
Workup
- temperaturethe mixture was cooled to ambient temperature
- concentrationconcentrated
- additiondiluted with water (50 mL)
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined organic layers were washed with brine (2×30 mL)
- dry with materialdried over Na2SO4
- filtrationfiltrated
- concentrationconcentrated
- customto give a residue, which
- customwas purified by chromatography on silica gel (dichloromethane/methanol=70:1)
Sources & evidence
- ORD record
- ord-336c95d72c284a2d8d01bb14f01b9405
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079930B2
Reaction notes
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