Dimethylformamide → 2-[6-(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)-5-hexynyloxy]benzenepropanoic acid methyl ester

HRID 327988

Reaction equation

[CH2:1]([C:4]1[C:13]2[O:12][CH2:11][CH2:10][C:9](=[O:14])[C:8]=2[CH:7]=[CH:6][C:5]=1OS(C(F)(F)F)(=O)=O)[CH2:2][CH3:3].[CH3:23][O:24][C:25](=[O:41])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]#[CH:40].C(N(CC)CC)C.CN(C)C=O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH3:23][O:24][C:25](=[O:41])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]#[C:40][C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:14])[CH2:10][CH2:11][O:12][C:13]=2[C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1.14 g (3.37 mmol) of 2,3-dihydro-8-propyl-7-[[(trifluoromethyl)sulfonyl]oxy]-4H-1-benzopyran-4-one, 0.94 g (3.62 mmol) of 2-[(5-hexynyl)oxy]benzenepropanoic acid methyl ester, 4.9 mL of dry triethylamine, 0.197 g (0.28 mmol) of dichlorobis(triphenylphosphine)palladium (II), and 21 mL of dry dimethylformamide was stirred and heated at 100° C. for 3 hr. The mixture was cooled, poured into ice-water, and worked-up with ether in the usual manner. The orange-red, oily residue was flash chromatographed on silica gel. Elution with 1:1 hexane-ether gave 1.25 g (83%) of 2-[6-(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)-5-hexynyloxy]benzenepropanoic acid methyl ester as a yellow oil.

Workup

temperatureThe mixture was cooled
customchromatographed on silica gel
washElution with 1:1 hexane-ether

Sources & evidence

ORD record: ord-30a5ea9899d74f578f909b473f4d3668
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05273999

Linked notes

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