Acetonitrile → HCID 58089020, compound

HRID 2277032Notes

Reaction equation

HRID 2277032 reaction equation
[Li]CCCC.[CH3:6][C:7]#[N:8].[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[C:20](OCC)=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([C:20](=[O:21])[CH2:6][C:7]#[N:8])[CH:25]=[CH:26][CH:27]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 12398517HCID 12398517, compoundHCID 178418339Butyllithium

Product 1

HCID 58089020HCID 58089020, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (1.6 M in hexanes, 146 mL, 234 mmol) was added dropwise at −78° C. to a solution of CH3CN (10.39 mL, 199 mmol) in THF (600 mL) and the reaction mixture was stirred for 30 min. A solution of ester (2) (30.0 g, 117 mmol) in THF (50 mL) was added and the mixture was further stirred for 30 min at −78° C. The reaction mixture was quenched at −78° C. by addition of aqueous NH4Cl (200 mL), diluted with EtOAc (500 mL), the organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 3-(3-(benzyloxy)phenyl)-3-oxopropanenitrile (3) as a pale yellow solid. Yield (25.0 g, 85%); 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 7.48-7.36 (m, 6H), 7.35-7.33 (m, 1H), 7.27-7.26 (m, 1H), 5.12 (s, 2H), 4.05 (s, 2H).

Workup

  1. stirringthe mixture was further stirred for 30 min at −78° C
  2. customThe reaction mixture was quenched at −78° C. by addition of aqueous NH4Cl (200 mL)
  3. additiondiluted with EtOAc (500 mL)
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-829aba0ca7994296ac1d3745b2225d11
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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