Pyridine → HCID 131715613, compound
Reaction equation
P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:20]Br.[C:22]([CH:28]([O:39][SiH:40]([CH3:42])[CH3:41])[CH2:29][C:30]1[CH:38]=[CH:37][C:33]([CH2:34][CH2:35]O)=[CH:32][CH:31]=1)([CH:25]([CH3:27])[CH3:26])([CH3:24])[CH3:23].N1C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>[C:22]([CH:28]([O:39][SiH:40]([CH3:42])[CH3:41])[CH2:29][C:30]1[CH:38]=[CH:37][C:33]([CH2:34][CH2:35][Br:20])=[CH:32][CH:31]=1)([CH:25]([CH3:27])[CH3:26])([CH3:24])[CH3:23]Participants
Procedure
To a stirred solution of (C6H5)3P (9.03 g, 34.4 mmol) in 220 ml of toluene at 0° C. was added bromine (1.76 ml, 34.4 mmol) over 10 minutes. To this stirred slurry was then added a solution of p-(2-thexyldimethylsilyloxyethyl)phenethyl alcohol (10.6 g, 34.4 mmol) and pyridine (2.78 ml, 34.4 mmol) in 50 ml of toluene over 10 minutes. This mixture was stirred at room temperature for 4 hours and diluted with 300 ml of saturated NaHCO3 solution. The resulting mixture was extracted with ether (4×300 ml). The combined ether extracts were dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated in 200 ml of hexane-ether 4:1 and filtered. The filtrate was concentrated and distilled under vacuum to give 9.9 g of p-(2-thexyldimethylsilyloxyethyl)phenethyl bromide (78%) as an oil.
Workup
- extractionThe resulting mixture was extracted with ether (4×300 ml)
- dry with materialThe combined ether extracts were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was triturated in 200 ml of hexane-ether 4:1
- filtrationfiltered
- concentrationThe filtrate was concentrated
- distillationdistilled under vacuum
Sources & evidence
- ORD record
- ord-aaee9b0358b14f76b84ca80730e763df
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04752616
Reaction notes
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