1-Nitropropane → 2-Nitro-1-phenyl-1-propanol

HRID 2107368ノート

反応式

HRID 2107368 の反応式
[Li]CCCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[N+:12]([CH2:15][CH2:16]C)([O-:14])=[O:13].C1C[O:21][CH2:20]C1>>[C:8]1([CH:20]([OH:21])[CH:15]([N+:12]([O-:14])=[O:13])[CH3:16])[CH:7]=[CH:6][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 4

HCID 79031-NitropropaneHCID 8028TetrahydrofuranHCID 8058HexaneHCID 178418339Butyllithium

生成物 1

HCID 2261182-Nitro-1-phenyl-1-propanol収率 28%

実験手順

n-BuLi (1.6 M hexane soln, 3.12 mL) was added dropwise with stirring to a solution of nitropropane (0.45 mL, 5 mmol) in THF (4 mL at -78° C. After 20 minutes the complex (as prepared above) was added and the solution allowed to warm to room temperature. After a further 4 hours the reaction was quenched at 0° C. with an aqueous slurry of disodium EDTA (1.86 g in 10 mL water). The mixture was diluted with water (50 mL) and extracted with Et2O (3×50 mL). The combined Et2O extracts were washed with hydrochloric acid (2 M, 50 mL), aqueous sodium bicarbonate (saturated, 50 mL) and water (50 mL, dried and evaporated in vacuo. Flash column chromatography [SiO2 hexane, Et2O 6:1] gave 1-phenyl-2-nitro-1-propanol (0.271 g, 28%) Erythro:threo ratio 4.6:1.

後処理

  1. customAfter 20 minutes the complex (as prepared above)
  2. additionwas added
  3. customAfter a further 4 hours the reaction was quenched at 0° C. with an aqueous slurry of disodium EDTA (1.86 g in 10 mL water)
  4. additionThe mixture was diluted with water (50 mL)
  5. extractionextracted with Et2O (3×50 mL)
  6. washThe combined Et2O extracts were washed with hydrochloric acid (2 M, 50 mL), aqueous sodium bicarbonate (saturated, 50 mL) and water (50 mL
  7. customdried
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-e6763ac6934e4b788bb63356b0dfc184
出典データセット
uspto-grants-1990_06
特許番号
US04933505

反応ノート

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