Water → HCID 56840382, compound

HRID 1410279Notes

Reaction equation

HRID 1410279 reaction equation
Br[CH2:2][CH3:3].[O:4]1[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[C:11]([C:14](=[O:24])[CH2:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])[CH:12]=[CH:13][C:5]1=2.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O.CCOCC>[O:4]1[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[C:11]([C:14](=[O:24])[CH:15]([CH2:2][CH3:3])[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:17])[CH:12]=[CH:13][C:5]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 825688HCID 825688, compound

Product 1

HCID 56840382HCID 56840382, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

Bromoethane (0.87 mmol) was added slowly to a solution 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-phenylpropane-1,3-dione (XX) (0.39 mmol) and K2CO3 (1.58 mmol) in DMSO (4 mL) stirred at room temperature under nitrogen. The solution was further stirred overnight at room temperature under nitrogen. The solution was poured into a mixture of water and ether. The etheric layer was separated, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to get 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-ethyl-3-phenylpropane-1,3-dione 17 as colorless viscous oil (35% yield). 1H NMR (DMSO-d6, 400 MHz): δ ppm 0.93 (t, J=7.4 Hz, 3H), 1.93 (m, 2H), 4.28 (m, 2H), 4.33 (m, 2H), 5.60 (t, J=6.5 Hz, 1H), 6.99 (d, J=8.6 Hz, 1H), 7.51-7.55 (m, 4H), 7.66 (m, 1H), 7.98 (d, J=7.3 Hz, 2H); ESIMS found C19H18O4 m/z 311 (M+H) and 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2-diethyl-3-phenylpropane-1,3-dione 18 as a white solids. ESIMS found C21H22O4 m/z 339 (M+H).

Workup

  1. customThe etheric layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-48ae68918eff43609bdec25663d99263
Source dataset
uspto-grants-2014_12
Patent number
US08921413B2

Reaction notes

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