Triethylamine → 6-((di-tert-Butylphosphino)methyl)-2,2'-bipyridine

HRID 2167163

反応式

HRID 2167163 の反応式
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]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 136643Phosphine, bis(1,1-dimethylethyl)-HCID 6428432,2'-Bipyridine, 6-(chloromethyl)-

生成物 1

HCID 532341466-((di-tert-Butylphosphino)methyl)-2,2'-bipyridine収率 85%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  1. customTo an oven dried 50 mL pressure vessel
  2. customequipped with magnetic stirring bar
  3. customThe flask was sealed
  4. temperatureAfter cooling
  5. additionwas added
  6. stirringthe reaction mixture was stirred at room temperature for 1 hr
  7. customThe solvents were removed under reduced pressure
  8. customto obtain a white solid
  9. washThe residue was washed with ether (3×20 mL)
  10. filtrationthe ether filtered
  11. customwas removed under reduced pressure
  12. customto yield a white solid
  13. customIt was recrystallized from MeOH at ca. −30° C.

出典と根拠

ORDレコード
ord-b309024d2e2b451fbcb6027f7fc5c0a6
出典データセット
uspto-grants-2015_06
特許番号
US09045381B2

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