Allyl Alcohol → HCID 22020945, compound

HRID 1793329Notes

Reaction equation

HRID 1793329 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8].[CH2:9](O)[CH:10]=[CH2:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[O:8][CH2:11][CH:10]=[CH2:9]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 27624284-CHLORO-3-HYDROXYPYRIDINE

Product 1

HCID 22020945HCID 22020945, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diazenedicarboxylic acid diethyl ester (0.1572 mol) in THF (163 ml) was added dropwise to a mixture of 4-chloro-3-pyridinol (0.1429 mol), 2-propen-1-ol (0.1572 mol) and triphenyl-phosphine (0.1572 mol) in THF (276 ml), that was cooled with an ice-water bath and under nitrogen flow. The formed mixture was stirred on the ice-water bath for 15 minutes and at room temperature overnight. The mixture was concentrated under vacuum and the residue was washed with a saturated Na2CO3− solution. The mixture was extracted with DCM and the separated organic layer was dried, filtered and the solvent was evaporated until dry. The residue was treated with DIPE and the formed solid was filtered off and discarded. The filtrate was evaporated until dry and the residue was treated with diethyl ether and the formed solid was filtered off and discarded again. The filtrate was evaporated until dry and the residue was purified by open column chromatography over silica gel (eluent: DCM/2-propanone 99/1;98/2). The product fractions were collected and the solvent was evaporated, yielding 7.9 g of 4-chloro-3-(2-propenyloxy)-pyridine (intermediate (44).

Workup

  1. temperaturewas cooled with an ice-water bath and under nitrogen flow
  2. concentrationThe mixture was concentrated under vacuum
  3. washthe residue was washed with a saturated Na2CO3− solution
  4. extractionThe mixture was extracted with DCM
  5. customthe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customuntil dry
  9. additionThe residue was treated with DIPE
  10. filtrationthe formed solid was filtered off
  11. customThe filtrate was evaporated
  12. customuntil dry
  13. additionthe residue was treated with diethyl ether
  14. filtrationthe formed solid was filtered off
  15. customThe filtrate was evaporated
  16. customuntil dry
  17. customthe residue was purified by open column chromatography over silica gel (eluent: DCM/2-propanone 99/1;98/2)
  18. customThe product fractions were collected
  19. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1cb28e245e6246579ac3aca6c012a0d0
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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