Benzophenone → HCID 11219495, compound

HRID 896825Notes

Reaction equation

HRID 896825 reaction equation
[C:1]([O:7][CH2:8][C@H:9]1[O:13][C:12](=[O:14])[CH:11]=[CH:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:29]([O:32][CH2:33][CH3:34])(=[O:31])C.C(Cl)(Cl)Cl>O1CCOC1>[C:1]([O:7][CH2:8][C@H:9]1[O:13][C:12](=[O:14])[CH2:11][C@@H:10]1[CH:29]1[O:32][CH2:33][CH2:34][O:31]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 3102BenzophenoneHCID 6212ChloroformHCID 8857Ethyl AcetateHCID 10954515HCID 10954515, compound

Product 1

HCID 11219495HCID 11219495, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 125861,3-DioxolaneSolvent

Procedure

A solution containing 29.0 mg (0.146 mmol) compound (2d) and 3.0 mg (0.016 mmol) benzophenone in 20 mL [1,3]-dioxolane was irradiated at 0° C. for 1.5 hours according to the general procedure. Column chromatography (silica gel 15 g, ethyl acetate in hexanes 40%) gave compound (3d) (37 mg. 93%) as a colorless solid, Rf=0.21, [α]25D 23.8°, c 1.0, CHCl3, IR (neat) 1785, 1740, 1210, 740 cm−1; 1H-NMR (400 MHz, CDCl3) δ: 1.21 (s, 9H), 2.57-2.60 (m, 1H), 2.67-2.75 (m, 2H), 3.91-3.93 (m, 2H), 4.01-4.04 (m, 2H), 4.37 (dd, 1H, J=4.2 Hz, J=12.2 Hz), 4.38 (dd, 1H, J=2.9 Hz, J=12.2 Hz), 4.69 (mc, 1H), 4.92 (d, 1H, J=3.6 Hz). 13C-NMR (100.6 MHz, CDCl3, Dept) δ: 27.14 (+), 29.75 (−), 38.70 (+) (quat), 65.26 (−), 65.43 (−), 65.58 (−), 77.37 (+), 103.30 (+), 175.47 (quat), 178.02 (quat). C13H20O6; Exact Mass: 272.13; Mol. Wt.: 272.29; C, 57.34, H, 7.40, O, 35.25.

Workup

  1. customwas irradiated at 0° C. for 1.5 hours

Sources & evidence

ORD record
ord-0d0c5cda8575438db8fcbd6ba52397cd
Source dataset
uspto-grants-2005_07
Patent number
US06919465B2

Reaction notes

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