tert-Butanol → HCID 11063236, compound

HRID 1597675Notes

Reaction equation

HRID 1597675 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.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[Cl-].[NH4+]>N.C1COCC1>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][C:3]1([C:2]#[N:9])[CH:8]=[CH:7][CH2:6][CH:5]=[CH:4]1)[CH3:21]

Participants

8

Reactant 5

HCID 6386tert-ButanolHCID 7505BenzonitrileHCID 7748Ethyl bromoacetateHCID 25517Ammonium ChlorideHCID 3028194Lithium

Product 1

HCID 11063236HCID 11063236, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium (0.17 g, 24 mmol) was added in portions to a 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 10 minutes, ethyl bromoacetate (2.2 mL, 3.3 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 (3×25 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), and concentrated under reduced pressure. Flash chromatography (SiO2. CH2Cl2) afforded 1.12 g (60%) 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 (3×25 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-b65df186dda14a4498f867b99f61be1b
Source dataset
uspto-grants-2001_09
Patent number
US06294690B1

Reaction notes

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