Water → HCID 57656229, compound

HRID 2041470Notes

Reaction equation

HRID 2041470 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][C:5]1([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[O:9][CH2:8][CH2:7][O:6]1.O>C1COCC1>[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][C:5]1([C:10]2[CH:11]=[CH:12][C:13]([CH2:14][NH2:15])=[CH:16][CH:17]=2)[O:9][CH2:8][CH2:7][O:6]1

Participants

4

Reactant 2

HCID 962WaterHCID 57656447HCID 57656447, compound

Product 1

HCID 57656229HCID 57656229, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 4-[2-(3,3-dimethyl-butyl)-[1,3]dioxolan-2-yl]-benzonitrile (271 mg, 1.046 mmol) in anhydrous THF (10 mL). Add under nitrogen 1M lithium aluminum hydride in THF (2.1 mL, 2.1 mmol) at 0° C. and stir the mixture at room temperature for 2 h. Cool to 0° C., add water and extract the aqueous phase twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain the desired intermediate as an oil (0.263 mg) that was used without any further purification.

Workup

  1. temperatureCool to 0° C.
  2. extractionextract the aqueous phase twice with EtOAc
  3. dry with materialDry the combined organic extracts over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d2056a7cef9142f5acafae8824018af7
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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