tert-Butanol → HCID 10900116, compound

HRID 1862582Notes

Reaction equation

HRID 1862582 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][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[Cl-].[NH4+]>N.C1COCC1>[C: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)([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 5

HCID 6386tert-ButanolHCID 7505BenzonitrileHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 3028194Lithium

Product 1

HCID 10900116HCID 10900116, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium (1.73 g, 249 mmol) was added in portions to a stirred solution of benzonitrile (10.2 mL, 10.3 g, 99.9 mmol) and t-BuOH (9.6 mL, 7.4 g, 100 mmol) in NH3 (50 mL) and THF (10 mL) under N2 at −78° C. After stirring for 25 minutes, t-butyl bromoacetate (29.5 mL, 39.0 g, 200 mmol) was added dropwise. After 1 hour, ammonium chloride (41.8 g, 781 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 (125 mL) was added and the mixture extracted with MTBE (3×50 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Flash chromatography (SiO2, CH2Cl2-1:14 MTBE:CH2Cl2) afforded 16.0 g (73%) of product as an oil.

Workup

  1. waitAfter 1 hour
  2. customwas removed with a stream of N2
  3. additionWater (125 mL) was added
  4. extractionthe mixture extracted with MTBE (3×50 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6360a34705194b6c85ffc04f6f9bf374
Source dataset
uspto-grants-2003_03
Patent number
US06538148B2

Reaction notes

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