Diisopropylamine → Methyl 5-bromo-2-methyl-2-phenyl-pentanecarboxylate

HRID 1167096

反応式

HRID 1167096 の反応式
C([Li])CCC.C(N[CH:10]([CH3:12])[CH3:11])(C)C.C1([CH:19](C)[C:20]([O:22][CH3:23])=[O:21])C=CC=CC=1.[Br:25][CH2:26][CH2:27][CH2:28]Br.[CH3:30][CH2:31][CH2:32][CH2:33][CH2:34]C>O1CCCC1>[Br:25][CH2:26][CH2:27][CH2:28][C:10]([CH3:11])([C:12]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:19][C:20]([O:22][CH3:23])=[O:21]

参加物

7

反応物 5

HCID 7912DiisopropylamineHCID 80011,3-DibromopropaneHCID 8058HexaneHCID 569653Methyl alpha-methylbenzeneacetateHCID 178418339Butyllithium

生成物 1

HCID 22995606Methyl 5-bromo-2-methyl-2-phenyl-pentanecarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

15 g (0.234 mol) of n-butyl lithium as a 2.5 molar solution in hexane are added dropwise to a solution of 32.8 ml (0.234 mol) of diisopropylamine in 200 ml of anhydrous tetrahydrofuran at −30° C. and stirred for 10 minutes at −10° C. 38.4 g (0.234 mol) of methyl 2-phenylpropionate are added dropwise at −76° C. and stirred for 30 minutes at this temperature. Then 26.3 ml (0.257 mol) of 1,3-dibromopropane are added, when the addition has ended the cooling bath is removed and the mixture is stirred for 14 hours at ambient temperature. The reaction solution is poured onto 1.2 l of water and extracted with diethylether. The organic phases are extracted with water, dried over sodium sulphate and the solvent is removed. The residue is distilled under high vacuum.

後処理

  1. stirringstirred for 30 minutes at this temperature
  2. additionwhen the addition
  3. customis removed
  4. stirringthe mixture is stirred for 14 hours at ambient temperature
  5. additionThe reaction solution is poured onto 1.2 l of water
  6. extractionextracted with diethylether
  7. extractionThe organic phases are extracted with water
  8. dry with materialdried over sodium sulphate
  9. customthe solvent is removed
  10. distillationThe residue is distilled under high vacuum

出典と根拠

ORDレコード
ord-17cecb85e5184900a32903ea401b91a3
出典データセット
uspto-grants-2003_09
特許番号
US06617325B1

関連ノート

読み込み中…