Propyne → HCID 67286863, compound

HRID 1020501Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH:11]([CH3:13])[CH3:12])[C:3]=1[S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH:22]#[C:23][CH3:24]>C(N(CC)CC)C.C(OCC)C.[Cu]I>[CH:11]([O:10][C:4]1[C:3]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:2]([C:22]#[C:23][CH3:24])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -40 °C

Procedure

A mixture of the product of Step A (0.123 g; 0.296 mmol), Cl2Pd(PPh3)2 (0.040 g; 0.057 mmol), CuI (0.014 g; 0.073 mmol) in anhydrous triethylamine (3 ml) was cooled to −40° C., degassed under reduced pressure and saturated with dry N2. The propyne gas (0.45 g; 11.2 mmol) was added to it at −40° C. The reaction flask was sealed with septum and allowed to warm up to room temperature and stirred for 3 h at room temperature and diluted to 20 ml with diethyl ether and solid precipitated, filtered off. The filtrate was evaporated to dryness under reduced pressure and the residue, purified by flash column chromatography (SiO2, hexane, hexane/ethyl acetate, 9:1) to give the title compound (0.065 g; 67% yield) as colourless syrup. 1H-NMR (CDCl3) 1.26 (d, 6H, J=6.17 Hz); 2.09 (s, 3H); 3.79 (s, 3H); 4.2 (s, 2H); 4.44 (m, 1H, J=6.17 Hz); 6.73 (d, 1H, J=8.53 Hz); 7.12 (d, 1H, J=8.53 Hz); 7.15-7.4 (m, 5H).

Workup

customdegassed under reduced pressure and saturated with dry N2
customThe reaction flask was sealed with septum
temperatureto warm up to room temperature
customprecipitated
filtrationfiltered off
customThe filtrate was evaporated to dryness under reduced pressure
customthe residue, purified by flash column chromatography (SiO2, hexane, hexane/ethyl acetate, 9:1)

Sources & evidence

ORD record: ord-c9d5407b6b6f477396149230d2a39ab7
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716335B2

Reaction notes

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