Tetrahydrofuran → tert-Butyl (2-chloro-4-formylpyridin-3-yl)carbamate

HRID 1914820ノート

反応式

HRID 1914820 の反応式
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1.CN(CCN(C)C)C.C([Li])CCC.[NH4+].[Cl-].C1C[O:34][CH2:33]C1>CCCCCC.CCOC(C)=O.CN(C=O)C>[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[C:6]([CH:33]=[O:34])[CH:5]=[CH:4][N:3]=1

参加物

9

反応物 5

HCID 8028TetrahydrofuranHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 11961738tert-Butyl (2-chloropyridin-3-yl)carbamateHCID 178418339Butyllithium

生成物 1

HCID 58034339tert-Butyl (2-chloro-4-formylpyridin-3-yl)carbamate

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-10 °C

実験手順

To a solution of tert-butyl (2-chloropyridin-3-yl)carbamate (7-2) (3.01 g, 13.2 mmol) and TMEDA (3.37 g, 29 mmol) in THF (50 mL) at −78° C. was added a 2.5 M solution of n-butyllithium in hexane (11.6 mL) dropwise over 10 minutes and the mixture was stirred for 1 hour. The mixture was warmed up to −10° C. and then cooled to −78° C. DMF (3.06 mL) was added to the mixture and then the mixture was warmed to ambient temperature over 3 hours. Saturated aq. NH4Cl and EtOAc were added to the mixture and the organic layer was washed with H2O and brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by silica gel chromatography (0-80% EtOAc/hexane) to give tert-butyl (2-chloro-4-formylpyridin-3-yl)carbamate (7-3) as a yellow solid.

後処理

  1. temperaturecooled to −78° C
  2. temperaturethe mixture was warmed to ambient temperature over 3 hours
  3. washthe organic layer was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (0-80% EtOAc/hexane)

出典と根拠

ORDレコード
ord-842791954b584bc2b78e77663e4a401e
出典データセット
uspto-grants-2013_12
特許番号
US08614221B2

反応ノート

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