α-(4-Bromophenyl)-1,3-dioxane-2-propanol → 4'-Bromo-3-(1,3-dioxan-2-YL)propiophenone
Reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:28])[CH2:20][CH2:21][CH:22]2[O:27][CH2:26][CH2:25][CH2:24][O:23]2)=[CH:15][CH:14]=1>ClCCl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:28])[CH2:20][CH2:21][CH:22]2[O:23][CH2:24][CH2:25][CH2:26][O:27]2)=[CH:15][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
PCC (8.16 g, 59.8 mmol) was admixed with 9 g SiO2 and ground (mortar & pestle) and suspended in Dichloromethane (360 mL). To the suspension was added in one portion Example J1, 1-(4-bromophenyl)-3-(1,3-dioxan-2-yl)propan-1-ol (9 g, 29.9 mmol) dissolved in 5 mL of the same solvent. The reaction mixture was stirred for 2 hours an filtered through celite (rinse with (CH2Cl2). After being concentrated the residue was charged (CH2Cl2) to a 40 M Biotage silica gel cartridge. Gradient elution 15-70% B over 750 mL mL (A=Hexanes; B=ethyl acetate) gave Example J2, 1-(4-bromophenyl)-3-(1,3-dioxan-2-yl)propan-1-one 7.7 g (86%). 1H NMR (500 MHz, CDCl3) δ 7.84 (d, J=8.7 Hz, 2H), 7.59 (d, J=8.5 Hz, 2H), 4.65 (t, J=4.9 Hz, 1H), 4.09-4.06 (m, 2H), 3.74 (dt, J=11.0, 2.4 Hz, 2H), 3.06 (t, J=7.3 Hz, 2H), 2.07-2.01 (m, 3H), 1.35-1.31 (m, 1H). LCMS: RT=1.9 minutes (condition 1); C13H15BrO3 Calcd.: 299; found: 299 (M+H)+.
Workup
- filtrationan filtered through celite (
- washrinse with (CH2Cl2)
- concentrationAfter being concentrated the residue
- additionwas charged (CH2Cl2) to a 40 M Biotage silica gel cartridge
- washGradient elution 15-70% B over 750 mL mL (A=Hexanes
Sources & evidence
- ORD record
- ord-49194603493d44f5a105f8dccbe4adf2
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846023B2
Reaction notes
Loading…