Sodium hydride → HCID 70691185, compound

HRID 1477280Notes

Reaction equation

HRID 1477280 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](Br)[CH:16]=[C:17]([CH2:19][CH2:20][CH:21]=[C:22]([CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[CH3:23])[CH3:18]>CN(C=O)C>[CH3:18]/[C:17](/[CH2:19][CH2:20]/[CH:21]=[C:22](\[CH3:23])/[CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])=[CH:16]\[CH2:15][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 550199Farnesyl bromide

Product 1

HCID 70691185HCID 70691185, 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 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 and the solution was kept stirring at 0° C. for 30 minutes. Farnesyl bromide (450 μL, 1.66 mmol) in 1 mL of anhydrous 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 at room temperature for 14 hours. The desired product was isolated via column chromatography using a solvent system of 100% Hexanes, 20:1 Hexanes:Ethyl acetate, 15:1 Hexanes:Ethyl acetate, 10:1 Hexanes:Ethyl acetate, 7:3 Hexanes:Ethyl acetate, and 2:1 Hexanes:Ethyl acetate. The purified product was characterized by NMR spectroscopy (1H-NMR, 13C-NMR) and high-resolution mass spectrometry (HRMS). 1H-NMR (300 MHz, CDCl3): δ 1.60-1.76 (12H), 1.96-2.12 (8H), 4.56 (d, 2H, J=6 Hz), 5.09 (m, 2H), 5.48 (t, 1H), 6.43 (d, 1H, J=9 Hz), 6.92-7.66 (4H); 13C-NMR (75 MHz, CDCl3): δ 15.93, 16.29, 17.70, 25.71, 26.29, 27.04, 39.53, 39.69, 109.75, 117.00, 117.83, 119.14, 123.31, 123.77, 128.33, 131.38, 135.56, 141.96, 143.27, 148.40, 155.33, 161.05. HRMS (CI) Calcd. for C24H31O3: 367.22733. found: 367.22801.

Workup

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

Sources & evidence

ORD record
ord-f71b2e76da4141699261ac1aa201e452
Source dataset
uspto-grants-2016_08
Patent number
US09403791B1

Reaction notes

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