Tributylstannane → Methallyltri-n-butyltin

HRID 1357499ノート

反応式

HRID 1357499 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([SnH:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].Br[CH2:27][C:28]([CH3:30])=[CH2:29]>C1COCC1>[CH3:29][C:28](=[CH2:27])[CH2:30][Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25]

参加物

6

反応物 4

HCID 5948TributylstannaneHCID 7912DiisopropylamineHCID 3577853-Bromo-2-methyl-1-propeneHCID 178418339Butyllithium

生成物 1

HCID 11013379Methallyltri-n-butyltin収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

n-Butyllithium (16.5 mL of a 2.5 M hexanes solution, 41.2 mmol)was added to a 0° C. solution of diisopropylamine (5.4 mL, 41.3 mmol) in THF (40 mL). After stirring for 5 minutes, tributyltin hydride (10 g, 34.4 mmol) was added. After stirring for 15 minutes at 0° C., the reaction mixture was cooled to −78° C. and 3-bromo-2-methylpropene (4.0 mL, 39.7 mmol) was added dropwise. After stirring for an additional hour, the cold reaction mixture was quenched with dilute ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate layer was dried (MgSO4), filtered and concentrated to afford a colorless liquid, 2-methylallyl tributyltin (11.6 g, 98%) which was used without purification for the next step.

後処理

  1. stirringAfter stirring for 15 minutes at 0° C.
  2. stirringAfter stirring for an additional hour
  3. customthe cold reaction mixture
  4. customwas quenched with dilute ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-49e350a24f5045468f17645b6d48838e
出典データセット
uspto-grants-2003_07
特許番号
US06593314B1

反応ノート

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