Sodium hydride → HCID 122429642, compound

HRID 1477282Notes

Reaction equation

HRID 1477282 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+].Br[CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23]>CN(C)C=O>[CH3:25][CH:18]([CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:16][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 1379141-Bromo-3,7-dimethyloctane

Product 1

HCID 122429642HCID 122429642, compound

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) (114 mg, 0.7 mmol) and 4 mL of anhydrous N,N-dimethylformamide (DMF) were added to the round bottom flask. The solution was stirred and cooled to 0° C. in a salt-ice bath. Sodium hydride (28 mg of 60% mineral oil suspension, 0.7 mmol) was added to the flask at which point the solution turned color from yellow to orange. The solution was kept stirring at 0° C. for 30 minutes. 1-Bromo-3,7-dimethyloctane (344.4 μL, 1.66 mmol) in 1 mL of DMF was 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 to warm back to room temperature over 14 hours. The desired product was obtained through preparatory thin layer chromatography using a 7:3 Hexanes:Ethyl acetate solvent system. The purified product was verified by NMR spectroscopy (1H-NMR, 13C-NMR) and high-resolution mass spectrometry (HRMS). 1H-NMR (300 MHz, CD3COCD3): δ 0.95-1.86 (19H), 4.08 (t, 2H), 6.40 (d, 1H, J=9 Hz), 7.17 (m, 2H), 7.27 (s, 1H), 7.92 (d, 1H, J=9 Hz); 13C-NMR (75 Hz, CD3COCD3): δ 19.91, 22.87, 22.97, 25.13, 25.37, 36.60, 37.92, 39.93, 67.54, 111.97, 117.58, 118.47, 120.28, 120.56, 129.10, 144.35, 149.19, 156.44, 160.77. FIRMS (EI) Calcd. for C19H26O3: 302.18820. found: 302.18871.

Workup

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

Sources & evidence

ORD record
ord-ebe9a7b551594fc4b630ef5cd932a610
Source dataset
uspto-grants-2016_08
Patent number
US09403791B1

Reaction notes

Loading…