Sodium hydride → 6-(((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)oxy)-2H-chromen-2-one

HRID 1477281Notes

Reaction equation

HRID 1477281 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[CH:5]2.[H-].[Na+].[CH2:15]([CH2:25]/[C:26](/[CH3:35])=[CH:27]/[CH2:28][CH2:29]/[C:30](/[CH3:34])=[CH:31]/[CH2:32]Br)/[CH:16]=[C:17](/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])\[CH3:18]>CN(C=O)C>[CH3:34]/[C:30](/[CH2:29][CH2:28]/[CH:27]=[C:26](\[CH3:35])/[CH2:25][CH2:15]/[CH:16]=[C:17](\[CH3:18])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:31]\[CH2:32][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 994776-hydroxy-2H-chromen-2-oneHCID 11175640HCID 11175640, compound

Product 1

HCID 1214599276-(((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)oxy)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

An oven-dried 50 mL round bottom flask was prepared with a magnetic stirring bar, a rubber septum cover, and a nitrogen inlet. 6-hydroxycoumarin (1) (474 mg, 2.92 mmol) and 4 mL of anhydrous DMF were added to the round bottom flask. The solution was stirred and cooled to 0° C. in a salt-ice bath. Sodium hydride (117 mg of 60% mineral oil suspension, 2.93 mmol) was added and the solution was stirred at 0° C. for 30 minutes. The crude geranylgeranyl bromide (302.85 mg) from the previous step was dissolved in anhydrous DMF, cooled to 0° C. and added drop-wise to the flask through the rubber septum using a syringe. The reaction mixture was left stirring under nitrogen at room temperature for 14 hours. The desired compound was isolated via preparative thin layer chromatography using a 7:3 Hexanes:Ethyl acetate solvent system. The purified product was characterized by 1H-NMR spectroscopy and high-resolution mass spectrometry (HRMS). 1H-NMR (300 MHz, CD3COCD3): δ 1.54-1.75 (15H), 1.93 (m, 12H), 4.65 (2H), 5.09 (3H), 5.53 (1H), 6.40 (1H), 7.11 (3H), 7.81 (1H). HRMS (EI) Calcd. for C79H38O3: 434.28210. found: 434.28236.

Workup

  1. customAn oven-dried 50 mL round bottom flask was prepared with a magnetic stirring bar
  2. stirringthe solution was stirred at 0° C. for 30 minutes
  3. temperaturecooled to 0° C.
  4. additionadded drop-wise to the flask through the rubber septum
  5. waitThe reaction mixture was left
  6. stirringstirring under nitrogen at room temperature for 14 hours

Sources & evidence

ORD record
ord-1bcd38e73e4342779b0318c552ba2d83
Source dataset
uspto-grants-2016_08
Patent number
US09403791B1

Reaction notes

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