Nitrogen → [5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-acetonitrile

HRID 1189397Notes

Reaction equation

HRID 1189397 reaction equation
N#N.Cl[CH2:4][C:5]1[S:9][C:8]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)=[CH:7][CH:6]=1.[C-:16]#[N:17].[Na+].O>CS(C)=O>[CH3:15][C:10]1([C:8]2[S:9][C:5]([CH2:4][C:16]#[N:17])=[CH:6][CH:7]=2)[O:14][CH2:13][CH2:12][O:11]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 8929Sodium CyanideHCID 668201882-(5-Chloromethyl-thiophen-2-yl)-2-methyl-[1,3]dioxolane

Product 1

HCID 67128699[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-methanol (10.00 g, 49.94 mmol) in dry CH2Cl2 (100 mL) was treated at 0° C. with Et3N (9.04 mL, 64.92 mmol) followed by DMAP (610 mg, 4.99 mmol) and Ms-Cl (4.65 mL, 59.92 mmol). After stirring at rt for 2 h, the reaction was quenched with water (200 mL). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give crude 2-(5-chloromethyl-thiophen-2-yl)-2-methyl-[1,3]dioxolane as a yellow oil. In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of this crude 2-(5-chloromethyl-thiophen-2-yl)-2-methyl-[1,3]dioxolane in DMSO (400 mL) was treated with sodium cyanide (9.07 g, 185.09 mmol) and the reaction mixture was stirred at 80° C. for 1 h. Water (400 mL) was added to the cooled reaction mixture and the product was extracted with EA (2×500 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA) gave the title compound: TLC: rf (60:40 hept-EA)=0.34. LC-MS-conditions 02: tR=0.89 min.

Workup

  1. extractionthe product was extracted with EA (2×500 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (60:40 hept-EA)

Sources & evidence

ORD record
ord-4aeab9cb1582420083d8787d4799cad3
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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