Water → tert-Butyl (R)-6-Cyano-5-hydroxy-3-oxohexanoate

HRID 5711ノート

反応式

HRID 5711 の反応式
[C:1]([CH2:3][C@@H:4]([O:16][Si](C(C)(C)C)(C)C)[CH2:5][C:6](=[O:15])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])#[N:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)C>O1CCCC1>[C:1]([CH2:3][C@@H:4]([OH:16])[CH2:5][C:6](=[O:15])[CH2:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])#[N:2]

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 15045171Hexanoic acid, 6-cyano-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-oxo-, 1,1-dimethylethyl ester, (R)-(9CI)

生成物 1

HCID 9794547tert-Butyl (R)-6-Cyano-5-hydroxy-3-oxohexanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A solution of crude (R)-1,1-dimethylethyl 6-cyano-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-oxohexanoate, 43 g (0.126 mol) in 350 mL of tetrahydrofuran is treated with 213 mL of tetrabutylammonium fluoride solution (1.0M in hexane). The resulting mixture is stirred for five hours, at 25° C. The mixture is treated with 500 mL of water, 300 mL of diethyl ether is added, and the layers separated. The organic layer is dried (magnesium sulfate) and then filtered through a plug of silica gel with the aid of anhydrous diethyl ether. The solvent is removed under a vacuum to obtain 21 g of crude (R)-1,1-dimethylethyl 6-cyano-5-hydroxy-3-oxohexanoate with acceptable NMR, MS and IR spectra.

後処理

  1. additionis added
  2. customthe layers separated
  3. dry with materialThe organic layer is dried (magnesium sulfate)
  4. filtrationfiltered through a plug of silica gel with the aid of anhydrous diethyl ether
  5. customThe solvent is removed under a vacuum

出典と根拠

ORDレコード
ord-a9e5e1fe7109474dbd63453d82efc8ef
出典データセット
uspto-grants-1993_09
特許番号
US05245047

反応ノート

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