Benzyl Alcohol → Benzyl 6-oxopyran-3-carboxylate

HRID 509409Notes

Reaction equation

HRID 509409 reaction equation
[CH:1]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][O:5][C:3](=[O:4])[CH:2]=1.[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C1COCC1.CN(C)C1C=CN=CC=1>[O:4]=[C:3]1[CH:2]=[CH:1][C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][O:5]1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 68141Coumalic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 325763Benzyl 6-oxopyran-3-carboxylate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of coumalic acid (1.2 g, 8.57 mmol) in DCM (20 mL) and THF (20 mL) was treated with 4-dimethylaminopyridine (0.105 g, 0.857 mmol). The reaction was stirred under nitrogen at 23° C. After 15 min, benzyl alcohol (0.886 mL, 8.57 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.642 g, 8.57 mmol) were added, and the stirring was continued. After 5 h, the solution was diluted with DCM (200 mL) and the mixture was washed with water (150 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 5-25% EtOAc/hexane), affording the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.32 (s, 1H), 7.80 (dd, J=9.78, 2.15 Hz, 1H), 7.33-7.48 (m, 5H), 6.33 (d, J=9.78 Hz, 1H), 5.31 (s, 2H). MS (ESI, positive ion) m/z: 231.1 (M+H).

Workup

  1. waitAfter 5 h
  2. washthe mixture was washed with water (150 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (eluent: 5-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-0813a332ade7413396fa08ddb3eda823
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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