3,3-Dimethyl-1-butanol → HCID 57656331, compound

HRID 2041506Notes

Reaction equation

HRID 2041506 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][OH:15].Cl[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][N:20]=1>C1COCC1>[CH3:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][O:15][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 122333,3-Dimethyl-1-butanolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 57656331HCID 57656331, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add sodium bis(trimethylsilyl)amide (3.95 mL, 7.9 mmol, 2M solution in THF) to a solution of 3,3-dimethyl-butan-1-ol (960 □L, 7.9 mmol) in anhydrous THF (10 mL). Stir for 30 min at room temperature and then add a solution of 6-chloro-nicotinonitrile (1 g, 7.2 mmol) in anhydrous THF (5 mL). Stir at room temperature overnight and then quench the reaction mixture with saturated aqueous NaHCO3 (100 mL). Extract the aqueous layer with dichloromethane (3×100 mL) and wash the organic layer with brine (100 mL). Dry the combined organic extracts over MgSO4 and concentrate in vacuo to give the desired intermediate as a yellow solid (1.4 g, 94%). GC-MS m/z: 204 (M+).

Workup

  1. stirringStir at room temperature overnight
  2. customquench the reaction mixture with saturated aqueous NaHCO3 (100 mL)
  3. extractionExtract the aqueous layer with dichloromethane (3×100 mL)
  4. washwash the organic layer with brine (100 mL)
  5. dry with materialDry the combined organic extracts over MgSO4
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-633a7e79351c4c139d31b42341fe981f
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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