Potassium Carbonate → Ethyl 2-(5-(heptan-4-ylcarbamoyl)benzo[d][1,3]dioxol-2-yl)acetate

HRID 339329Notes

Reaction equation

HRID 339329 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1)[CH2:5][CH2:6][CH3:7].C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:27][C:28](=[O:31])[C:29]#[CH:30])[CH3:26]>CC(C)=O>[CH3:1][CH2:2][CH2:3][CH:4]([NH:8][C:9]([C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH:30]([CH2:29][C:28]([O:27][CH2:25][CH3:26])=[O:31])[O:17][C:12]=2[CH:11]=1)=[O:18])[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12182Ethyl propiolateHCID 66772665N-(heptan-4-yl)-3,4-dihydroxybenzamide

Product 1

HCID 57527998Ethyl 2-(5-(heptan-4-ylcarbamoyl)benzo[d][1,3]dioxol-2-yl)acetateYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(heptan-4-yl)-3,4-dihydroxybenzamide (example 18a) (0.29 mmol, 75 mg) was dissolved in dry acetone with 6 eq excess (242 mg) of potassium carbonate then 1.2 eq excess (36 μl) of propynoic acid ethyl ester was added and a mixture was refluxed for 24 h. The solvent was evaporated and a solid was dissolved in dichloromethane and extracted with 10% NaHCO3 and water. The crude product was purified by chromatography on silica gel to give 72 mg of desired product (71%). 1H NMR (500 MHz, CDCl3): δ 0.91-0.94 (t, 6H), L23-1.30 (m, 4H), 1.37-1.41 (4H), 2.97-2.98 (d, 2H), 3.70-3.74 (dd, 2H), 4.12-4.17 (m, 1H), 4.2-4.24 (m, 3H), 5.61-5.64 (d, 1H), 6.58-6.60 (t, 1H), 6.79-6.81 (d, 1H), 7.23 (s, 1H), 7.60-7.85 (b, 1H). MS (M+H, 350.1).

Workup

  1. temperaturea mixture was refluxed for 24 h
  2. customThe solvent was evaporated
  3. dissolutiona solid was dissolved in dichloromethane
  4. extractionextracted with 10% NaHCO3 and water
  5. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3968f4e9bc874495ad0272316023483d
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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