Vanillin → HCID 86653390, compound

HRID 1192776Notes

Reaction equation

HRID 1192776 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[C:12](O)(=[O:34])/[CH:13]=[CH:14]\[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl.O>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:8]=1[O:9][C:12](=[O:34])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:2]=[O:1]

Participants

7

Reactant 3

HCID 1183VanillinHCID 10868DicyclohexylcarbodiimideHCID 86653387HCID 86653387, compound

Product 1

HCID 86653390HCID 86653390, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of vanillin (330 mg, 2.17 mmol), cis-docosahexaenoic acid (870 mg, 2.65 mmol) and catalytic amount of 4-(dimethylamino)pyridine in dichloromethane (15 mL) was added a solution of N,N′-dicyclohexylcarbodiimide (720 mg, 3.50 mmol) in DCM (5 mL) for 5 min at ice cold temperature. The mixture was stirred at rt for 16 h and diluted with water. DCM layer was separated and the aqueous layer was extracted with DCM (3×100 mL). The combined DCM layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and the residue was chromatographed over silica gel column using hexane-ethyl acetate (95:5) mixture as an eluent to give the product as an oil (800 mg, 80%). 1H NMR (400 MHz, CDCl3) δ 9.94 (1H, s, —CHO), 7.49 (1H, d, J=1.6 Hz, H-2), 7.47 (1H, dd, J=8.0, 1.6 Hz, H-6), 7.20 (1H, d, J=8.0 Hz, H-5), 5.30-5.48 (12H, m, H-4′, 5′, 7′, 8′, 10′, 11′, 13′, 14′, 16′, 17′, 19′, 20′, 3.89 (3H, s, —OCH3), 2.80-2.88 (10H, m, H-6′, 9′, 12′, 15′, 18′), 2.58-2.67 (2H, m, H-2′), 2.22-2.25 (2H, m, H-21′), 2.05-2.11 (2H, m, H-3′), 0.97 (3H, t, J=7.4 Hz, H-22′).

Workup

  1. customDCM layer was separated
  2. extractionthe aqueous layer was extracted with DCM (3×100 mL)
  3. washThe combined DCM layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customthe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-82f24fffde764833a283db495cdbac61
Source dataset
uspto-grants-2014_03
Patent number
US08680143B2

Reaction notes

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