tert-Butanol → HCID 54210642, compound

HRID 1862580Notes

Reaction equation

HRID 1862580 reaction equation
[Li].[C:2](#[N:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(O)(C)C.[CH2:15]([O:22][C:23](=[O:26])[CH2:24]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>N.C1COCC1>[CH2:15]([O:22][C:23](=[O:26])[CH2:24][C:3]1([C:2]#[N:9])[CH:8]=[CH:7][CH2:6][CH:5]=[CH:4]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 6386tert-ButanolHCID 7505BenzonitrileHCID 25517Ammonium ChlorideHCID 62576Benzyl bromoacetateHCID 3028194Lithium

Product 1

HCID 54210642HCID 54210642, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium (0.17 g, 24 mmol) was added in portions to a stirred solution of benzonitrile (0.99 mL, 1.0 g, 9.7 mmol) and t-BuOH (0.93 mL. 0.72 g, 9.7 mmol) in NH3 (50 mL) and THF (10 mL) under N2 at −78° C. After stirring for 15 minutes, benzyl-2-bromoacetate (3.1 mL, 4.5 g, 20 mmol) was added dropwise. After 1 hour, ammonium chloride (4.0 g, 75 mmol) was added in portions. The reaction mixture was slowly warmed to room temperature while the NH3 was removed with a stream of N2. Water (25 mL) was added, and the mixture extracted with EtOAc (3×5 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), and concentrated under reduced pressure. Flash chromatography (SiO2, 1:1-3:1 CH2Cl2:hexane) afforded 1.79 g (73%) of product as an oil.

Workup

  1. waitAfter 1 hour
  2. customwas removed with a stream of N2
  3. additionWater (25 mL) was added
  4. extractionthe mixture extracted with EtOAc (3×5 mL)
  5. washThe combined organic extracts were washed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-838342becca548dda94dbeb47f330be4
Source dataset
uspto-grants-2003_03
Patent number
US06538148B2

Reaction notes

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