Tetrahydro-4H-pyran-4-one → HCID 59016635, compound

HRID 339460Notes

Reaction equation

HRID 339460 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][NH2:9])=[O:7].[O:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>CCOCC.C(O)(=O)C.C(Cl)Cl.CO>[O:14]1[CH2:19][CH2:18][C:17](=[N:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=2[CH3:13])[CH2:16][CH2:15]1

Participants

7

Reactant 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 450912733-Methoxy-2-methylbenzohydrazide

Product 1

HCID 59016635HCID 59016635, compoundYield 83.5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-methoxy-2-methyl-benzoic acid hydrazide (4.14 g, 23 mmol) was suspended in a mixture of 80 mL of ether, 40 mL of CH2Cl2 and 2 drops of acetic acid. A solution of tetrahydro-pyran-4-one (2.3 g, 23 mmol) in 20 mL of CH2Cl2 and 2-3 mL of methanol were added, and the mixture was refluxed for 10 minutes. The reaction mixture was allowed to cool and was concentrated to about 80 mL. Pentane (100 mL) was added, resulting in the formation of a precipitate. The suspension was chilled in a freezer and filtered to yield 5.04 g of 3-methoxy-2-methyl-benzoic acid (tetrahydro-pyran-4-ylidene)-hydrazide as a tan, flocculent, semi-crystalline material. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.2 (t, 1H), 6.98 (d, 1H), 6.95 (d, 1H), 3.9 (t, 2H), 3.86 (s, 3H), 3.8 (t, 2H), 2.65 (t, 2H), 2.42 (t, 2H), 2.35 (s, 3); Rf=0.15 (3:1 ethyl acetate:hexane).

Workup

  1. temperaturethe mixture was refluxed for 10 minutes
  2. temperatureto cool
  3. concentrationwas concentrated to about 80 mL
  4. additionPentane (100 mL) was added
  5. customresulting in the formation of a precipitate
  6. temperatureThe suspension was chilled in a freezer
  7. filtrationfiltered

Sources & evidence

ORD record
ord-870d3464993c4f19b847799d792ceb02
Source dataset
uspto-grants-2014_11
Patent number
US08895306B2

Reaction notes

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