Diisobutylaluminum hydride → HCID 66727644、化合物

HRID 1361218ノート

反応式

HRID 1361218 の反応式
[Br:1][C:2]1[CH:6]=[C:5](/[CH:7]=[N:8]/[S:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[O:4][N:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[CH:6]=[C:5]([CH2:7][NH:8][S:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[O:4][N:3]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 87126736HCID 87126736、化合物

生成物 1

HCID 66727644HCID 66727644、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a chilled (−78° C.) yellow solution of 2-methyl-propane-2-sulfinic acid 1-(3-bromo-isoxazol-5-yl)-meth-(E)-ylideneamide (129 mg, 0.462 mmol) in THF (7 mL) was added a 1 M solution of DIBAH (1.2 mL, 1.2 mmol) in hexanes dropwise. After 1.5 hours, the reaction was quenched with MeOH (4 mL) and the cold bath was removed. The mixture was concentrated in vacuo and the residue was treated with 1 N aqueous NaOH (10 mL) and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 2-methyl-propane-2-sulfinic acid (3-bromo-isoxazol-5-ylmethyl)-amide which was used without further purification. MS m/z 281.35 (M), 283.32 (M+2).

後処理

  1. customthe reaction was quenched with MeOH (4 mL)
  2. customthe cold bath was removed
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue was treated with 1 N aqueous NaOH (10 mL)
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-480fd23a7f15466e89fa074529d4c5d8
出典データセット
uspto-grants-2011_02
特許番号
US07879873B2

反応ノート

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