Ethyl Acetate → HCID 69216503, compound

HRID 898678Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH2:23]Br)[CH:22]=2)[O:19][C:18]([CH3:26])([CH3:25])[CH2:17][C:16]3([CH3:28])[CH3:27])=[CH:7][CH:6]=1.[CH3:30][Si:31]([C:34]#[CH:35])([CH3:33])[CH3:32].C(OCC)(=O)C>C(N(CC)CC)C.CN(C)C=O.CCCCCC.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>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH2:23][C:35]#[C:34][Si:31]([CH3:33])([CH3:32])[CH3:30])[CH:22]=2)[O:19][C:18]([CH3:26])([CH3:25])[CH2:17][C:16]3([CH3:28])[CH3:27])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of {4-[8-bromomethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester (Compound 47, 1.1 g, 2.4 mmol) in triethyl amine (2 mL) and N,N-dimethylformamide (10 mL) was sparged with argon and treated with trimethylsilylacetylene (2 mL, 14.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.135 g, 0.192 mmol). The resulting reaction mixture was heated at 95° C. for 20 h at the end of which it was cooled to ambient temperature and subjected to flash column chromatography over silica gel (230-400 mesh) using 1-7% ethyl acetate in hexane as the eluent to afford the title compound as an oil (0.715 g, 63%). 1H NMR (300 MHz, CDCl3): δ7.49 (d, 1H, J=2.1 Hz), 7.47 (d, 2H, J=8.2 Hz), 7.37 (d, 1H, J=2.1 Hz), 7.25 (d, 2H, J=8.2 Hz), 3.70 (s, 3H), 3.63 (s, 2H) 3.55 (s, 2H), 1.83 (s, 2H), 1.35 (s, 6H), 1.34 (s, 6H), 0.20 (s, 9H).

Workup

customThe resulting reaction mixture
temperaturewas cooled to ambient temperature

Sources & evidence

ORD record: ord-e0b06cf82cad41fbb4d49a309b8ae378
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351737B2

Reaction notes

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