4-Iodobenzonitrile → 3-[2-(4-Cyanophenyl)-ethynyl]-2,5-dimethoxy-tetrahydrofuran

HRID 613868Notes

Reaction equation

[CH3:1][O:2][CH:3]1[CH:7]([C:8]#[C:9][Sn](CCCC)(CCCC)CCCC)[CH2:6][CH:5]([O:23][CH3:24])[O:4]1.I[C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:30]([C:29]1[CH:32]=[CH:33][C:26]([C:9]#[C:8][CH:7]2[CH2:6][CH:5]([O:23][CH3:24])[O:4][CH:3]2[O:2][CH3:1])=[CH:27][CH:28]=1)#[N:31]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,5-dimethoxy-3-(2-tributylstannylethynyl)-tetrahydrofuran (1.86 g, 4.18 mmol), 4-iodobenzonitrile (1.15 g, 5.02 mmol), and tetrakis(triphenylphosphine) palladium(0) (145 mg, 0.125 mmol) in toluene (25 mL) was heated at 100° C. After 5.5 hours, the resultant red solution was allowed to cool, and the solvent was removed under reduced pressure. Flash column chromatography twice with 10% EtOAc/hex provided 1.10 g (100%) of 3-[2-(4-cyanophenyl)-ethynyl]-2,5-dimethoxy-tetrahydrofuran as an orange oil. A mixture of diastereomers was observed by 1H NMR, which was used without further purification. 1H NMR (CDCl3): 3.12 (ddd, J=2.8, 6.6, 9.0 Hz), 2.57 (ddd, J=5.6, 9.3, 13.4 Hz), 2.08 (dd, J=2.5, 4.7 Hz), 2.04 (dd, J=3.1, 4.3 Hz). IR: 2227, 1603, 1216, 1102, 1012, 841 cm-1. Anal. Calculated for C15H15NO3.0.1 EtOAc: C, 69.51; H, 5.98; N, 5.26. Found: C, 69.52; H, 5.76; N, 5.32.

Workup

temperatureto cool
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-25a2bd132c41476994bbeb2951874ae9
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008243

Reaction notes

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