Ammonium Chloride → tert-Butyl 3-(3-benzyloxypropyl)-6-[3-(2,2-dimethylpropyl)cyclobutyl]-4-oxo-5-hexynoate

HRID 1912074ノート

反応式

HRID 1912074 の反応式
Br[C:2](Br)=[CH:3][CH:4]1[CH2:7][CH:6]([CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5]1.C([Li])CCC.[CH2:19]([O:26][CH2:27][CH2:28][CH2:29][CH:30]([C:39](=[O:44])NCOC)[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:19]([O:26][CH2:27][CH2:28][CH2:29][CH:30]([C:39](=[O:44])[C:2]#[C:3][CH:4]1[CH2:7][CH:6]([CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5]1)[CH2:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 71114707tert-Butyl 6-benzyloxy-3-(methoxymethylcarbamoyl)hexanoateHCID 86675042HCID 86675042、化合物HCID 178418339Butyllithium

生成物 1

HCID 71127328tert-Butyl 3-(3-benzyloxypropyl)-6-[3-(2,2-dimethylpropyl)cyclobutyl]-4-oxo-5-hexynoate収率 67.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1-(2,2-dibromovinyl)-3-(2,2-dimethylpropyl)cyclobutane (5 g) and tetrahydrofuran (50 mL) were mixed. To the mixture was added n-butyllithium (1.65 M in hexane) (20.5 mL) dropwise at −78° C. The mixture was stirred at ice temperature for 30 min. and a solution of tert-butyl 6-benzyloxy-3-(methoxymethylcarbamoyl)hexanoate (4.13 g) in tetrahydrofuran (25 mL) was added dropwise to the mixture. After stirring at ice temperature for 20 min., saturated aqueous ammonium chloride was added to the reaction mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/20) to give the title compound (3.45 g).

後処理

  1. stirringAfter stirring at ice temperature for 20 min.
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/20)

出典と根拠

ORDレコード
ord-8e1c1b07880a44fe903b7f1f9a09e891
出典データセット
uspto-grants-2013_12
特許番号
US08604069B2

反応ノート

読み込み中…