Water → HCID 86663282, compound

HRID 1038316Notes

Reaction equation

HRID 1038316 reaction equation
[Si]([O:8][CH2:9][C:10]([CH2:17][O:18][Si](C(C)(C)C)(C)C)([CH3:16])[C:11](=[O:15])[CH2:12][C:13]#[N:14])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[OH:8][CH2:9][C:10]([CH2:17][OH:18])([CH3:16])[C:11](=[O:15])[CH2:12][C:13]#[N:14]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86663283HCID 86663283, compound

Product 1

HCID 86663282HCID 86663282, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-4-methyl-3-oxopentanenitrile (1 equivalent) in anhydrous THF at 0° C. is added tetrabutylammonium fluoride (1-5 equivalents) and stirring is continued at rt until the reaction is substantially complete as determined by LCMS or TLC. Water is added followed by extraction with EtOAc. The extracts 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-(hydroxymethyl)-4-methyl-3-oxopentanenitrile.

Workup

  1. customis continued at rt until the reaction
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe extracts 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-c488e7983ed145aead2539cb0db65940
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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