tert-Butyl hydroperoxide → HCID 10379699, compound

HRID 1784158Notes

Reaction equation

[C:1]1([S:7]([C:10]2[CH:16]=[CH:15][C@H:14]([CH3:17])[C@H:13]([OH:18])[C@@H:12]([CH3:19])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:24]O)(C)(C)C>C1C=CC=CC=1.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[C:1]1([S:7]([C:10]2[C@H:16]3[C@H:15]([O:24]3)[C@H:14]([CH3:17])[C@H:13]([OH:18])[C@@H:12]([CH3:19])[CH:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of dienyl sulfone 32 (67 mg, 0.24 mmol), molybdenum hexacarbonyl (3 mg, 0.01 mmol), and tert-butylhydroperoxide (74 μL of 5M solution in decane) in benzene (3 mL) was heated at 80° C. for 10 h. The reaction mixture was concentrated via rotary evaporation, purified by flash column chromatography (ethyl acetate/hexanes; 50:50) to afford 62 mg (88% yield) of epoxide α36 as a light yellow solid. mp 137.0-139.0° C.; [α]20D=+59.3 (c=0.51, CH2Cl2); 1H NMR (CDCl3, 300 MHz) δ 7.93-7.96 (m, 2H), 7.58-7.70 (m, 3H), 7.39 (d, J=7.2 Hz, 1H), 3.90 (dd, J=4.5 Hz, 1.5 Hz, 1H), 3.64 (br s, 1H), 3.42 (m, 1H), 3.05-3.15 (m, 2H), 2.55 (tq, J=2.1 Hz, 7.2 Hz, 1H), 1.39 (d J=7.2 Hz, 3H), 1.18 (d, J=7.5 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 147.9, 139.7, 136.5, 133.9, 129.7, 128.2, 78.3, 65.5, 52.5, 41.5, 32.2, 17.4, 17.2; Analytical. Calculated for C15H18O4S: C, 61.20; H, 6.16. Found: C, 60.95; H, 6.07.

Workup

concentrationThe reaction mixture was concentrated via rotary evaporation
custompurified by flash column chromatography (ethyl acetate/hexanes; 50:50)

Sources & evidence

ORD record: ord-86f49c24746b4b3a8725423ba5400fa9
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501535B2

Reaction notes

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