Hydrochloric Acid → HCID 86716174, compound

HRID 512151Notes

Reaction equation

HRID 512151 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11](OC)(=[O:14])[CH:12]=[CH2:13].CC(C)([O-:20])C.[K+].Cl.[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>>[CH3:26][O:27][C:28]([C:24]1[CH2:25][C:8]([C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([C:9]#[N:10])[CH2:13][CH2:12][C:11]=1[OH:14])=[O:20]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 8028TetrahydrofuranHCID 14751282-(6-Chloropyridin-3-yl)acetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 86716174HCID 86716174, compound

Conditions

Temperature
-65 °C

Procedure

To a solution of 2-(6-chloro-3-pyridinyl)acetonitrile (4.3 g, 28 mmol, purchased from Matrix Scientific, Columbia, S.C., USA) and methyl acrylate (4.8 g, 56 mmol) in dry THF (150 mL) cooled to −65° C. was added solid potassium tert-butoxide (7.9 g, 70 mmol) under nitrogen atmosphere. The reaction mixture was stirred at −65° C. for 45 minutes. The reaction mixture was then acidified with 3 N HCl and extracted with DCM (3×150 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give crude 5-(6-chloro-pyridin-3-yl)-5-cyano-2-hydroxy-cyclohex-1-enecarboxylic acid methyl ester which was used in the next step without purification (6.0 g, 75%).

Workup

  1. extractionextracted with DCM (3×150 mL)
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9cc055950a8241ef970e634bb37b5ee9
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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