tert-Butanol → Tert-butyl 3-bromobutanoate

HRID 2167903ノート

反応式

HRID 2167903 の反応式
[Br:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:21](O)([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[C:21]([O:5][C:4](=[O:6])[CH2:3][CH:2]([Br:1])[CH3:7])([CH3:24])([CH3:23])[CH3:22]

参加物

5

反応物 3

HCID 6386tert-ButanolHCID 9845Trifluoroacetic anhydrideHCID 1028603-Bromobutanoic acid

生成物 1

HCID 57092335Tert-butyl 3-bromobutanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The required 3-bromobutyric acid tert-butyl ester was prepared as follows: To a solution of 3-bromobutyric acid (5.0 mL; 47.0 mmol) in tetrahydrofuran (50 mL) was added dropwise trifluoroacetic anhydride (13.7 mL; 98.7 mmol) at −40° C. After 1 hour at −40° C. tert-butyl alcohol (20 mL) was added. The resulting mixture was allowed to warm to RT and stirred overnight. Subsequently, the reaction mixture was concentrated in vacuo. The residue was treated with 2M aqueous NaOH solution and extracted with Et2O. The organic layer was dried (Na2SO4), and concentrated in vacuo to afford 3-bromobutyric acid tert-butyl ester (6.05 g), which was used as such.

後処理

  1. customThe required 3-bromobutyric acid tert-butyl ester was prepared
  2. concentrationSubsequently, the reaction mixture was concentrated in vacuo
  3. additionThe residue was treated with 2M aqueous NaOH solution
  4. extractionextracted with Et2O
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f34bebdf5cb848be8bb0e4189ef93676
出典データセット
uspto-grants-2015_06
特許番号
US09045441B2

反応ノート

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