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

HRID 1198360Notes

Reaction equation

HRID 1198360 reaction equation
[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]

Participants

6

Reactant 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)

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-60527e64f54245f688ae4e6b570ba6ca
Source dataset
uspto-grants-1994_01
Patent number
US05280126

Reaction notes

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