Tributylphosphine → 1-[4-(6-Bromo-pyridin-2-ylmethoxy)-2-hydroxy-3-propyl-phenyl]-ethanone

HRID 2267021Notes

Reaction equation

HRID 2267021 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[OH:10][C:11]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15](O)[CH:14]=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][C:15]2[CH:14]=[CH:13][C:12]([C:21](=[O:23])[CH3:22])=[C:11]([OH:10])[C:16]=2[CH2:17][CH2:18][CH3:19])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 866198461-[4-(6-Bromo-pyridin-2-ylmethoxy)-2-hydroxy-3-propyl-phenyl]-ethanoneYield 44.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Combine (6-bromo-pyridin-2-yl)-methanol (1.00 g, 5.32 mmol), 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (1.033 g, 5.32 mmol) and tri-n-butylphosphine (1.46 mL, 5.85 mmol, Aldrich Chemical Co.) in tetrahydrofuran (5.3 mL), add 1,1′-(azodicarbonyl)dipiperidine (1.48 g, 5.85 mmol, Aldrich Chemical Co.). After 12 hours at ambient temperature, add diethyl ether (white precipitate forms) and filter, collect liquid and remove solvents under reduced pressure. Purify residue by flash chromatography to obtain the title compound as a white solid (854 mg, 2.35 mmol): MS (m/z): 286 (M−Br+1).

Workup

  1. filtrationfilter
  2. customcollect liquid
  3. customremove solvents under reduced pressure

Sources & evidence

ORD record
ord-b90ddf1fa35a42fe90b38bb7244e5e41
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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