Hydrochloric Acid → ethyl (3-{3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]propyl}phenoxy)-acetate

HRID 2389380Notes

Reaction equation

HRID 2389380 reaction equation
[H-].[Li+].[C:3]1([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=1)[O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].Cl>CN(C=O)C>[C:3]1([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][C:13](=[O:16])[N:14]([CH2:24][CH2:25][CH2:26][C:27]3[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=3)[O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:15]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 62714Lithium hydrideHCID 227488105-(Diphenylmethyl)-2-pyridoneHCID 86637892Ethyl [3-(3-iodopropyl)phenoxy]acetate

Product 1

HCID 59145362ethyl (3-{3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]propyl}phenoxy)-acetateYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of LiH (6.20 g) in DMF (100 mL) was added a solution of 5-(diphenylmethyl)-2(1H)-pyridinone (82.4 g) in DMF (500 mL) at ambient temperature. A solution of ethyl [3-(3-iodopropyl)phenoxy]acetate (118 g) in DMF (300 mL) was added dropwise to the mixture at ambient temperature over 30 minutes and the mixture was stirred at the same temperature for 24 hours. The resulting mixture was poured into 1M HCl aqueous solution (800 mL) at 0° C. and the mixture was extracted with EtOAc (2 L+1 L). The organic layer was washed successively with 12% NaCl aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1) to afford ethyl (3-{3-[5-(diphenylmethyl)-2-oxo-1(2H) -pyridinyl]propyl}phenoxy)-acetate(113 g) as a slightly yellow oil.

Workup

  1. extractionthe mixture was extracted with EtOAc (2 L+1 L)
  2. washThe organic layer was washed successively with 12% NaCl aqueous solution and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-15612b04ce5c4cb2aa9877d8b0534770
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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