Acetic Acid → ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

HRID 535145Notes

Reaction equation

HRID 535145 reaction equation
C1(C(=[N:14][CH:15]([CH2:21][CH:22]=[C:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.O.C(O)(=O)C>C1COCC1>[NH2:14][CH:15]([CH2:21][CH:22]=[C:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 58313138ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

Product 1

HCID 58313060ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoateYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate (162) (6.8 g, 18.0 mmol) in THF (30 mL) was added water (30 mL) and glacial acetic acid (20 mL) and the reaction stirred at room temperature for 2.5 h. The reaction was concentrated in vacuo and the residue dissolved in 0.1 N HCl. It was extracted twice with ethyl acetate and the organic layer was discarded. To the aqueous layer was added solid potassium carbonate until the solution gave blue pH paper. The aqueous layer was extracted with 15% isopropanol/dichloromethane (3×) and the organic layer dried over sodium sulfate and concentrated in vacuo to afford the title compound as a clear oil (3.05 g, 79% yield).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue dissolved in 0.1 N HCl
  3. extractionIt was extracted twice with ethyl acetate
  4. additionTo the aqueous layer was added solid potassium carbonate until the solution
  5. customgave blue pH paper
  6. extractionThe aqueous layer was extracted with 15% isopropanol/dichloromethane (3×)
  7. dry with materialthe organic layer dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e396090a48b4426b00260435c99b6b5
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

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