Ethyl Acetate → HCID 86757339, compound

HRID 651879Notes

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][CH:24]=C)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[O:35]C(C)=O>C1COCC1.O>[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][CH:24]=[O:35])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 81 (44 mg, 81 μmol) in THF (3 mL) was treated sequentially with a solution of NaIO4 (35 mg, 162 μmol, 2 equiv) in 0.5 mL H2O and a solution of OSO4 (7.5 mM in THF, 0.53 mL, 4 μmol, 0.05 equiv). The reaction mixture was stirred for 6 h at 25° C. EtOAc (20 mL) was added and the organic layer was dried (Na2SO4), filtered through Celite, and the solvent removed under vacuum. Chromatography (SiO2, 1×15 cm, 15% EtOAc-hexane) afforded 110 (35 mg, 80%) as an oil: 1H NMR (CDCl3, 400 MHz) δ 9.73 (t, J=1.3 Hz, 1H), 8.32 (d, J=8.2 Hz, 1H), 8.20 (d, J=8.4 Hz, 1H), 7.61-7.49 (m, 4H), 7.42-7.32 (m, 3H), 6.77 and 6.72 (two s, 1H), 5.32-5.25 (m, 2H), 3.86 (ddd, J=14.0, 8.6 Hz, 6.7 Hz, 1H), 3.47 (m, 1H), 2.48 (m, 2H), 1.93-1.75 (m, 2H), 1.29 and 1.23 (two s, 9H); IR (film) νmax 3064, 3032, 2975, 2930, 2722, 1638, 1616, 1590, 1407, 1160 cm31 1; FABHRMS (NBA-CsI) m/z 678.0095 (M+Cs+, C26H28INO4 requires 678.0117).

Workup

dry with materialthe organic layer was dried (Na2SO4)
filtrationfiltered through Celite
customthe solvent removed under vacuum

Sources & evidence

ORD record: ord-d8fc0739f82a4d2ba60a7964d87707e1
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06281354B1

Reaction notes

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