HCID 59603146, compound → HCID 59603182, compound

HRID 2061365Notes

Reaction equation

HRID 2061365 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][C:8]=1[CH:9]=O)C>C(O)(=O)C>[CH3:18][O:17][C:12]1[CH:13]=[C:14]([O:15][CH3:16])[C:7]2[O:6][C:5]([CH:4]=[O:3])=[CH:9][C:8]=2[CH:11]=1

Participants

3

Reactant 1

HCID 59603146HCID 59603146, compound

Product 1

HCID 59603182HCID 59603182, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 39 (1.2 g, 4.0 mmol) in acetic acid (35 mL) was refluxed for 16 h. After cooling, the solution was evaporated to dryness. The crude product was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (2:1) to give 40 (230 mg, 28%) as a white solid. 1H NMR (500 MHz, CDCl3): δ: 9.89 (1H, s, CHO), 7.50 (1H, s, H-3), 6.69 (1H, d, J4,6=2.2 Hz, H-6), 6.64 (1H, d, J4,6=2.2 Hz, H-4), 4.01 (3H, s, OMe), 3.87 (3H, s, OMe). 13C NMR CDEPT 135, (500 MHz, CDCl3): δ: 179.91 (CHO), 153.37 (C-2), 116.10 (C-3), 101.80 (C-6), 94.90 (C-4), 56.20 (OMe), 55.88 (OMe).

Workup

  1. temperatureAfter cooling
  2. customthe solution was evaporated to dryness
  3. custompurified by flash chromatography
  4. washeluting with hexane/EtOAc (2:1)

Sources & evidence

ORD record
ord-09f3453b49a34e24a5a2f1eb97ef929e
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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