Tetrahydrofuran → HCID 11137946, compound

HRID 1066372Notes

Reaction equation

HRID 1066372 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Li][CH2:10][CH2:11][CH2:12]C.C(N1CCCCC1)=[O:15].C1C[O:25][CH2:24][CH2:23]1>>[CH3:8][C:7]1[C:2](/[CH:12]=[CH:11]/[C:10]([O:25][CH2:24][CH3:23])=[O:15])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 174291-PiperidinecarboxaldehydeHCID 2208322-Bromo-3-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 11137946HCID 11137946, compound

Procedure

To a solution of 2-bromo-3-methylpyridine (10.36 g; 60.2 mmol) in 120 mL of THF at −100° C. was added dropwise a 1.6 M solution of n-BuLi (65.6 mmol). After 20 min of stirring at that temperature, 1-formylpiperidine (7.65 g) in 10 mL of THF was added and the solution was warmed to r.t.. After 30 min of stirring at r.t., triethyl phosphonoacetate (13.7 mL; 69.1 mmol) was added dropwise below 30° C. After 1 h of stirring, the mixture was quenched with NH4OAc (25%) and extracted with EtOAc. The solvent was removed and the crude oil was purified by silica gel chromatography (25% EtOAc in hexane) to yield 10.32 g of the title compound.

Workup

  1. additionwas added
  2. stirringAfter 1 h of stirring
  3. customthe mixture was quenched with NH4OAc (25%)
  4. extractionextracted with EtOAc
  5. customThe solvent was removed
  6. customthe crude oil was purified by silica gel chromatography (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-eb9d71eefb464ef28e46a5fbac1e1858
Source dataset
uspto-grants-2001_06
Patent number
US06242493B1

Reaction notes

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