Acetonitrile → HCID 90406336, compound

HRID 2277039Notes

Reaction equation

HRID 2277039 reaction equation
[CH3:1][C:2]#[N:3].[Li]CCCC.[O:9]1[CH2:14][CH2:13][CH:12]([CH2:15][O:16][C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20](OC)=[O:21])[CH2:11][CH2:10]1>C1COCC1>[O:21]=[C:20]([C:19]1[CH:24]=[CH:25][CH:26]=[C:17]([O:16][CH2:15][CH:12]2[CH2:11][CH2:10][O:9][CH2:14][CH2:13]2)[CH:18]=1)[CH2:1][C:2]#[N:3]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 90404905HCID 90404905, compoundHCID 178418339Butyllithium

Product 1

HCID 90406336HCID 90406336, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The solution of CH3CN (0.37 g, 8.9 mmol) in THF (40 mL) was added to n-BuLi (1.6 M in hexanes, 0.58 g, 8.9 mmol) at −78° C. and the reaction mixture was stirred for 30 min. Solution of ester (12) (1.5 g, 5.9 mmol) in THF (10 mL) was added to the reaction mixture and the resulting solution was further stirred for 30 min. The reaction mixture was quenched by addition of aq.NH4Cl (200 mL) and extracted with EtOAc (100 mL). Drying over anhydrous Na2SO4 and concentration under reduced pressure gave 3-oxo-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propanenitrile (13). Yield (1.5 g, 96%); 1H NMR (400 MHz, DMSO-d6) δ 7.43-7.37 (m, 3H), 7.26-7.21 (m, 1H), 4.75 (bs, 2H), 3.89-3.83 (m, 4H), 3.32 (t, J=11.6 Hz, 2H), 2.03-1.98 (m, 1H), 1.69-1.66 (m, 2H), 1.38-1.28 (m, 2H).

Workup

  1. stirringthe resulting solution was further stirred for 30 min
  2. customThe reaction mixture was quenched by addition of aq
  3. extractionNH4Cl (200 mL) and extracted with EtOAc (100 mL)
  4. dry with materialDrying over anhydrous Na2SO4 and concentration under reduced pressure

Sources & evidence

ORD record
ord-3b1585ecc0964ea19bf02ad226c9b7c7
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

Loading…