Benzophenone → HCID 60018519, compound

HRID 896827Notes

Reaction equation

HRID 896827 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@H:9]1[O:13][C:12](=[O:14])[CH:11]=[CH:10]1.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>[O:31]1[CH2:34][CH2:33][O:32][CH:29]1[C@@H:10]1[C@@H:9]([CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[O:13][C:12](=[O:14])[CH2:11]1

Participants

6

Reactant 4

HCID 3102BenzophenoneHCID 6212ChloroformHCID 8857Ethyl AcetateHCID 14432036HCID 14432036, compound

Product 1

HCID 60018519HCID 60018519, compound

Reagents, catalysts & solvents 1

HCID 125861,3-DioxolaneSolvent

Procedure

A solution containing 136 mg (0.686 mmol) compound (2f) and 18.7 mg (0.103 mmol) benzophenone in 100 mL [1,3]-dioxolane was irradiated at 20° C. for 5.75 hours according to the general procedure. Column chromatography (silica gel 40 g, ethyl acetate in hexanes 60%) gave compound (3f) as two diastereomers (170 mg, 91%) as a colorless oil, Rf=0.25, [α]25D −129°, c 0.8, CHCl3. 1H-NMR (300 MHz, CDCl3) δ: 1.38-1.82 (m, 6H), 2.40-2.46 (m, 1H), 2.60-2.75 (m, 2H), 3.39-3.48 (m, 1H), 3.61-3.70 (m, 1H), 3.75-3.81 (m, 2H), 3.84-3.87 (m, 2H), 3.93-3.98 (m, 2H), 4.53-4.63 (m, 2H), 4.86-4.89 (m, 1H). 13C-NMR (75.4 MHz, CDCl3, Dept) diastereomer A: δ: 18.72 (−), 25.20 (−), 29.98 (−), 30.02 (−), 40.08 (+), 61.52 (−), 64.68 (−), 65.33 (−), 68.33 (−), 78.98 (+), 98.21 (+), 103.64 (+), 176.51 (quat); B: δ: 19.23 (−), 25.20 (−), 30.21 (−), 30.24 (−), 40.08 (+), 62.20 (−), 65.05 (−), 65.45 (−), 68.81 (−), 79.08 (+), 99.09 (+), 103.71 (+), 176.72 (quat). C13H20O6; Exact Mass: 272.13; Mol. Wt.: 272.29; C, 57.34; H, 7.40; O, 35.25.

Workup

  1. customwas irradiated at 20° C. for 5.75 hours

Sources & evidence

ORD record
ord-e19bc835c2e243c29d411f855d875e65
Source dataset
uspto-grants-2005_07
Patent number
US06919465B2

Reaction notes

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