Tetrahydrofuran → N-(4-(2-Hydroxyethylidene)cyclohexyl)acetamide

HRID 404257

Reaction equation

HRID 404257 reaction equation
[H-].[Na+].O=[C:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:13])[CH3:12])[CH2:6][CH2:5]1.C1C[O:17][CH2:16][CH2:15]1>>[OH:17][CH2:16][CH:15]=[C:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:13])[CH3:12])[CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 538565N-(4-Oxocyclohexyl)acetamide

Product 1

HCID 58294115N-(4-(2-Hydroxyethylidene)cyclohexyl)acetamide

Procedure

To a stirred suspension of sodium hydride (1.2 mmol) in THF was added triethyl phosphonoacetate (1.2 mmol) drop wise. The mixture was allowed to stir until it became colorless and a solution of N-(4-oxocyclohexyl)acetamide (1.0 mmol) in THF (1 mL) was added. The solution was allowed to stir at rt until the reaction was complete (by TLC). The solvent was removed under reduced pressure and the crude residue was filtered through a small plug of silica gel to afford the desired product, which was used directly in the next synthetic step.

Workup

  1. stirringto stir at rt until the reaction
  2. customThe solvent was removed under reduced pressure
  3. filtrationthe crude residue was filtered through a small plug of silica gel

Sources & evidence

ORD record
ord-891f331053f1428a847cc69c037e3ac3
Source dataset
uspto-grants-2014_06
Patent number
US08748469B2

Linked notes

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