Dimethyl oxalate → HCID 68182629, compound

HRID 524394Notes

Reaction equation

HRID 524394 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[CH:9][C:10]([S:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:11][CH:12]=1.[C:19](OC)(=[O:24])[C:20]([O:22][CH3:23])=[O:21].[NH4+].[Cl-]>C(OCC)C>[CH:14]1([S:13][C:10]2[N:11]=[CH:12][C:7]([C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:8][CH:9]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 11120Dimethyl oxalateHCID 25517Ammonium ChlorideHCID 62721387HCID 62721387, compoundHCID 178418339Butyllithium

Product 1

HCID 68182629HCID 68182629, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Under anhydrous condition n-BuLi (1.6 M solution in hexane, 5.08 mL, 8.13 mmol) was added to stirred solution of 5-bromo-2-cyclopentylsulfanyl-pyridine (2.0 g, 8.13 mmol) in 15 mL dry diethyl ether at −78° C. and stirred for 20 minutes. A solution of dimethyl oxalate (1.09 g, 9.30 mmol) in 15 mL of dry diethyl ether was added dropwise with the help of syringe and resulted reaction mixture was allowed to warm slowly to 0° C. within 1 hr. Reaction mixture was poured on aq. saturated solution of NH4Cl (25 mL), mixture was then extracted with (3×50 mL) diethyl ether; organic layer was washed with brine, dried over anhydrous sodium sulfate, sodium sulfate was filtered and washed with diethyl ether and solvent was removed under reduced pressure. The crude material was purified by silica-gel column chromatography (3 to 5% ethyl acetate in hexane) to afford pure compound (0.5 g).

Workup

  1. customresulted
  2. customreaction mixture
  3. customReaction mixture
  4. extractionwas then extracted with (3×50 mL) diethyl ether
  5. washorganic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate, sodium sulfate
  7. filtrationwas filtered
  8. washwashed with diethyl ether and solvent
  9. customwas removed under reduced pressure
  10. customThe crude material was purified by silica-gel column chromatography (3 to 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d44d2e0846e6453ea69d67d047d38339
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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