Tetrahydrofuran → HCID 86757340, compound

HRID 651880Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([I:19])=[C:11]([N:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][CH2:22][CH2:23]C=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:52][C:53]([O:55][CH3:56])=[O:54])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:57]1COCC1>>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([I:19])=[C:11]([N:20]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:21][CH2:22][CH2:23]/[CH:57]=[CH:52]/[C:53]([O:55][CH3:56])=[O:54])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

HCID 86757339HCID 86757339, compound

Product 1

HCID 86757340HCID 86757340, compoundYield 63%

Conditions

Temperature: 25 °C

Procedure

A solution of 110 (13.3 mg, 24.4 μmol) in THF (0.3 mL) was treated with methyl (triphenylphosphoranylidene)acetate (23.9 mg, 71.5 μmol, 3 equiv). The reaction mixture was stirred for 48 h at 25° C. and the solvent removed under vacuum. Chromatography (SiO2, 10-25% EtOAc-hexane gradient elution) afforded 112 (9 mg, 14 mg theoretical, 63%) as an oil: 1H NMR (CDCl3, 400 MHz) δ 8.32 (d, J=8.2 Hz, 1H), 8.20 (d, J=8.2 Hz, 1H), 7.61-7.48 (m, 5H), 7.42-7.32 (m, 2H), 6.91 (m, 1H), 6.74 and 6.64 (two s, 1H), 5.79 (d, J=15.5 Hz, 1H), 5.31-5.23 (m, 2H), 3.81 (ddd, J=14.0, 9.6, 3.6 Hz, 1H), 3.70 (s, 3H), 3.35 (m, 1H), 2.18 (m, 2H), 1.75-1.55 (m, 2H), 1.29 and 1.24 (two s, 9H); IR (film) νmax 2975, 2947, 1702, 1658, 1471, 1391, 1366, 1307, 1272, 1162 cm−1.

Workup

customthe solvent removed under vacuum
washChromatography (SiO2, 10-25% EtOAc-hexane gradient elution)

Sources & evidence

ORD record: ord-22d0e8ba76c646078aa0470710a2d574
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06281354B1

Reaction notes

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