Tetrahydrofuran → HCID 71281816, compound

HRID 1481783Notes

Reaction equation

HRID 1481783 reaction equation
Cl[C:2]1[N:17]=[CH:16][C:15]([I:18])=[C:14](Cl)[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[Na].[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH2:23]([O:24][C:2]1[N:17]=[CH:16][C:15]([I:18])=[C:14]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[C:22]1[CH:21]=[CH:25][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 5360545SodiumHCID 89421783HCID 89421783, compound

Product 1

HCID 71281816HCID 71281816, compoundYield 51%

Procedure

Into a solution of benzyl 2,4-dichloro-5-iodonicotinate (3.7 g, 9.1 mmol) in THF (20 mL) was added a solution of sodium benzoxide in THF (1.0 M×20 mL, 20 mmol). The mixture was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl. The mixture was extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, evaporated and purified by silica chromatography (0-7% ethyl acetate in hexanes) to give benzyl 2,4-bis(benzyloxy)-5-iodonicotinate (2.55 g, 51%).

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. custompurified by silica chromatography (0-7% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6440c10b690349c89ea5d1a60fdf85b3
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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