4-Methoxybenzyl alcohol → HCID 22607567, compound

HRID 2307832Notes

Reaction equation

HRID 2307832 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]O)=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 22607567HCID 22607567, compoundYield 53%

Procedure

To a solution of 3-chloro-5-hydroxypyridine (2.0 g, 17.0 mmol), 4-methoxybenzyl alcohol (2.85 g, 25.5 mmol) and triphenylphosphine (6.68 g, 25.5 mmol) in dry THF (100 ml) DEAD (4.44 g, 25.5 mmol) was added dropwise. The resulting solution was stirred 3 hours at room temperature. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed (brine), dried (Na2SO4), filtered and concentrated under vacumm. Purification on silica gel with 20% ethyl acetate/hexane to provide the title compound (1.9 g, 53%). MS (DCI/NH3) m/e 250 (M+1)+.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacumm
  6. customPurification on silica gel with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1ab57c159d074a6596b3fb65eeb1097b
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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