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

HRID 705427Notes

Reaction equation

HRID 705427 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-72bbb327ed704c298243c30a6e3bbc83
Source dataset
uspto-grants-2015_11
Patent number
US09174942B2

Reaction notes

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