Methanol → HCID 67128426, compound

HRID 1189398Notes

Reaction equation

HRID 1189398 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH2:14][C:15]#N)=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.CO.[OH-:19].[K+].[OH2:21]>>[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH2:14][C:15]([OH:21])=[O:19])=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

6

Reactant 5

HCID 887MethanolHCID 947NitrogenHCID 962WaterHCID 14797Potassium HydroxideHCID 67128699[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-acetonitrile

Product 1

HCID 67128426HCID 67128426, compound

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]-acetonitrile (2.67 g, 12.77 mmol) in a 1:1 mixture of MeOH and H2O (11 mL) was treated at rt with KOH (1.43 g, 25.54 mmol). After stirring at reflux for 1.5 h, the cooled reaction mixture was washed with ether. The aq. phase was carefully acidified to pH 4-5 with 1M HCl and the product was extracted several times with CH2CL2. The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a brown oil. LC-MS-conditions 02: tR=0.79 min.

Workup

  1. temperatureat reflux for 1.5 h
  2. customthe cooled reaction mixture
  3. washwas washed with ether
  4. extractionthe product was extracted several times with CH2CL2
  5. dry with materialextracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-524e07e80d384b12b0c4d86977daf5e6
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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