Water → HCID 86663286, compound

HRID 1038321Notes

Reaction equation

HRID 1038321 reaction equation
[O:1]=[C:2]([C:6]([CH2:25][O:26][Si](CC)(CC)CC)([CH2:16][O:17][Si](CC)(CC)CC)[CH2:7][O:8][Si](CC)(CC)CC)[CH2:3][C:4]#[N:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[OH:26][CH2:25][C:6]([CH2:7][OH:8])([CH2:16][OH:17])[C:2](=[O:1])[CH2:3][C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86663287HCID 86663287, compound

Product 1

HCID 86663286HCID 86663286, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-oxo-5-(triethylsilyloxy)-4,4-bis((triethylsilyloxy)methyl)pentanenitrile (1 equivalent) in anhydrous THF at 0° C. is added tetrabutylammonium fluoride (1-5 equivalents) then stirring is continued at rt until the reaction is substantially complete as monitored by LCMS or TLC. Water is added followed by extraction with EtOAc. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography to afford 5-hydroxy-4,4-bis(hydroxymethyl)-3-oxopentanenitrile.

Workup

  1. customis continued at rt until the reaction
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c5a6bfd1fcb7441ba5ef75d7675c2059
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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