Triethylamine → HCID 18319566, compound

HRID 1699371Notes

Reaction equation

I[C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O)=[O:19].C(N(CC)CC)C>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 2,3-dihydro-9-iodo-1-benzoxepin-4-carboxylate (1.03 g), 2-formylbenzeneboronic acid (0.49 g), tetrakis(triphenylphosphine)palladium(0) (0.35 g), and triethylamine (0.92 ml) in N,N-dimethylformamide (10.3 ml) was stirred at 100° C. under nitrogen atomsphere for 2.5 hours and partitioned between ethyl acetate and water. The organic layer was washed successively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by medium pressure liquid chromatography (silica gel) using a mixture of ethyl acetate and n-hexane (1:30˜1:9) to give a solid of ethyl 2,3-dihydro-9-(2-formylphenyl)-1-benzoxepin-4-carboxylate (0.63 g).

Workup

custompartitioned between ethyl acetate and water
washThe organic layer was washed successively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated in vacuo
customThe residue was purified by medium pressure liquid chromatography (silica gel)
additiona mixture of ethyl acetate and n-hexane (1:30˜1:9)

Sources & evidence

ORD record: ord-0de6433d70db486e9fa52765f2a87ac6
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346527B1

Reaction notes

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