Water → 5-tert-butyldimethylsilyl-2,2-dimethyl-3(S)hydroxy-pentane-nitrile

HRID 900498Notes

Reaction equation

HRID 900498 reaction equation
[Si:1]([CH2:8][CH2:9][C@H:10]([O:16]C(=O)C)[C:11]([CH3:15])([CH3:14])[C:12]#[N:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].O>C(O)C>[Si:1]([CH2:8][CH2:9][C@H:10]([OH:16])[C:11]([CH3:15])([CH3:14])[C:12]#[N:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23567930HCID 23567930, compound

Product 1

HCID 235679315-tert-butyldimethylsilyl-2,2-dimethyl-3(S)hydroxy-pentane-nitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

4.8 g (16 mmol) of 5-tert-butyldimethylsilyl-2,2-dimethyl-3(S)-acetoxy-pentane-nitrile is dissolved in 50 ml of ethanol and mixed with 1.28 g of NaOH (32 mmol). It is stirred for 3 hours at 25° C., added to 200 ml of water, extracted with 2×200 ml of MTB ether, dried on sodium sulfate and concentrated by evaporation.

Workup

  1. extractionextracted with 2×200 ml of MTB ether
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-25d91916068d4c19a320341a0eda47de
Source dataset
uspto-grants-2008_04
Patent number
US07358382B2

Reaction notes

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