Triethylamine → Tert-butyl 3-(3-((trimethylsilyl)ethynyl)phenethoxy)propanoate

HRID 909889Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(CC)CC)C.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29]>C(OCC)(=O)C.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.[Cu]I>[CH3:27][Si:28]([C:31]#[C:32][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 100 °C

Procedure

tert-Butyl 3-(3-bromophenethoxy)propanoate (1.5 g), triethylamine (6 mL), trimethylsilylacetylene (1.92 mL), Pd(Ph3P)4 (0.26 g) and copper (I) iodide (0.04 g) was sealed into a microwave tube. The reaction was heated to 100° C. over a period of 5 min in the microwave reactor. The reaction mixture was diluted with ethyl acetate and filtered through a pad of Celite and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0-10% ethyl acetate in isohexane to afford tert-butyl 3-(3-((trimethylsilyl)ethynyl)phenethoxy)propanoate as a yellow liquid (1.56 g). 1H NMR (300 MHz, CDCl3) δ 7.41-7.12 (m, 4H), 3.67 (t, J=6.3 Hz, 2H), 3.63 (t, J=7.1 Hz, 2H), 2.83 (t, J=7.1 Hz, 2H), 2.47 (t, J=6.5 Hz, 2H), 1.44 (s, 9H), 0.24 (s, 9H).

Workup

filtrationfiltered through a pad of Celite
customevaporated
customto afford crude product
customThe crude product was purified by flash silica chromatography, elution gradient 0-10% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-de43d32fe969448da249840390fb6c17
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017602B2

Reaction notes

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