Triethylamine → 6-((di-tert-Butylphosphino)methyl)-2,2'-bipyridine
Reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=1.[C:15]([PH:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CO>[C:15]([P:19]([CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=1)[C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])([CH3:17])[CH3:16]Participants
Conditions
- Temperature
- 50 °C
Procedure
To an oven dried 50 mL pressure vessel equipped with magnetic stirring bar was added 6-chloromethyl-2,2′-bipyridine (BPy-CH2Cl) (2.05 g, 10.00 mmol), di-tert-butyl phosphine (1.75 g, 12.00 mmol), and 30 mL MeOH in a nitrogen glove box. The flask was sealed and heated at 50° C. for 48 hrs with stirring outside the glove box. After cooling, it was reintroduced to the glove box, triethylamine (1.82 g, 18.00 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr. The solvents were removed under reduced pressure to obtain a white solid. The residue was washed with ether (3×20 mL) and the ether filtered and was removed under reduced pressure to yield a white solid. It was recrystallized from MeOH at ca. −30° C. to yield 2.67 g (85%) of 6-di-tert-butylphosphinomethyl-2,2′-bipyridine (BPy-tPNN).
Workup
- customTo an oven dried 50 mL pressure vessel
- customequipped with magnetic stirring bar
- customThe flask was sealed
- temperatureAfter cooling
- additionwas added
- stirringthe reaction mixture was stirred at room temperature for 1 hr
- customThe solvents were removed under reduced pressure
- customto obtain a white solid
- washThe residue was washed with ether (3×20 mL)
- filtrationthe ether filtered
- customwas removed under reduced pressure
- customto yield a white solid
- customIt was recrystallized from MeOH at ca. −30° C.
Sources & evidence
- ORD record
- ord-b309024d2e2b451fbcb6027f7fc5c0a6
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045381B2
Reaction notes
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