Triethyl phosphonoacetate → Ethyl 2-(1-benzylpiperidin-4-ylidene)acetate

HRID 64309Notes

Reaction equation

HRID 64309 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:17]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:17]([N:24]1[CH2:29][CH2:28][C:27](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydride

Product 1

HCID 10377866Ethyl 2-(1-benzylpiperidin-4-ylidene)acetateYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of NaH (318 mg, 7.94 mmol) in THF (20 mL) was added a solution of ethyl 2-(diethoxyphosphoryl)acetate (1.78 g, 7.94 mmol) in THF (5 mL) dropwise over 30 min at 0° C. After stirring for 10 min, a solution of 1-benzylpiperidin-4-one (1.0 g, 5.29 mmol) in THF (5 mL) was added dropwise at 0° C. over 20 min. The mixture was allowed to stir for 60 min. Then, the reaction was quenched with water (10 mL). The mixture was extracted with EA (10 mL×3). The combined organic layers were dried over Na2SO4, concentrated and purified by chromatography column on silica gel using 25% of EA in PE as eluant to give the product (1.2 g, 87.3%) as a yellow oil. MS (ESI, m/e) [M+1]+ 260.0.

Workup

  1. stirringto stir for 60 min
  2. customThen, the reaction was quenched with water (10 mL)
  3. extractionThe mixture was extracted with EA (10 mL×3)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by chromatography column on silica gel using 25% of EA in PE as eluant

Sources & evidence

ORD record
ord-7d7b722ee7d9436dbe3caa36e37603e1
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

Loading…