Water → HCID 59019312, compound

HRID 911649Notes

Reaction equation

HRID 911649 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14].[C:17]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)#[N:18].O>O1CCOCC1>[CH3:11][C:12]([CH3:16])([CH3:15])[CH2:13][O:14][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([C:17]#[N:18])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6404Neopentyl alcoholHCID 869964-(Bromomethyl)benzonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 59019312HCID 59019312, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

Add sodium bis(trimethylsilyl)amide (3 mL, 6 mmol, 2M solution in THF) to a solution of 2,2-dimethyl-1-propanol (528 mg, 6 mmol) in anhydrous 1,4-dioxane. Stir until the suspension becomes homogenous. Then add a solution of 4-cyanobenzyl bromide (980 mg, 5 mmol) in anhydrous 1,4-dioxane (3 mL). Heat the mixture in a microwave oven at 100° C. for 30 min. Cool to room temperature, add water (50 mL) and extract with EtOAc (3×50 mL). Dry the combined organic extracts over MgSO4, and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (95:5 to 1:1 gradient) to obtain the desired intermediate (811 mg, 80%).

Workup

  1. temperatureCool to room temperature
  2. extractionextract with EtOAc (3×50 mL)
  3. dry with materialDry the combined organic extracts over MgSO4
  4. concentrationconcentrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (95:5 to 1:1 gradient)

Sources & evidence

ORD record
ord-fafd5e3b8c27469e9e9004c02c09cb16
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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