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

HRID 968931Notes

Reaction equation

HRID 968931 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-025e8494c4564f40940d4e3cc5b959eb
Source dataset
uspto-grants-2007_12
Patent number
US07304162B2

Reaction notes

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