Potassium Carbonate → HCID 57871402, compound

HRID 550221Notes

Reaction equation

HRID 550221 reaction equation
Br[CH:2]([CH2:9][CH3:10])[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[CH3:11][O:12][C:13]([C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:25]([CH2:36][CH3:37])([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH3:35])[CH:29]=3)[CH2:26][CH3:27])[CH:21]=2)[CH:16]=1)=[O:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH3:11][O:12][C:13]([C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:25]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH:2]([CH2:9][CH3:10])[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5])=[C:30]([CH3:35])[CH:29]=3)([CH2:36][CH3:37])[CH2:26][CH3:27])[CH:21]=2)[CH:16]=1)=[O:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 57871411HCID 57871411, compoundHCID 85970701HCID 85970701, compound2×

Product 1

HCID 57871402HCID 57871402, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

Add 4-bromo-2,2-dimethylhexane-3-one (660 mg, 3.187 mmol) to a mixture of 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester (1.1 g, 3.035 mmol), and K2CO3 (629 mg, 4.55 mmol) in DMF (10 ml). Maintain the reaction mixture 45° C. for 14 h. Add an additional amount of 4-bromo-2,2-dimethylhexane-3-one (314 mg, 1.52 mmol) and maintain the mixture at 60° C. while stirring for 62 h. Cool the reaction mixture and dilute it with CH2Cl2, filter, and concentrate in vacuo. Chromatograph the resulting residue (CH2Cl2to 1% EtOAc/CH2Cl2) to give the title compound as a colorless viscous oil (1.299 g, 88%). 1NMR (400 MHz, CDCl3) δ ppm: 0.62 (t, J=7.2 Hz, 6H), 1.01 (t, J=7.6 Hz, 3H), 1.16 (s, 9H), 1.88 (m, 2H), 2.16 (m, 4H), 2.19 (s, 3H), 3.97 (s, 3H), 4.86 (dd, J=5.2, 1.6 Hz, 1H), 6.53 (d, J=8.4 Hz, 1H), 6.88 (m, 2H), 7.14 (dd, J=7.2, 1.6 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.82 (s, 1H), 7.85 (d, J=8.8 Hz, 1H), 8.04 (dd, J=6.4, 2.0 Hz, 1H), 8.52 (s, 1H). High Res. ES-MS: 511.2824; calc. for C32H40O4+Na: 511.2825.

Workup

  1. temperaturemaintain the mixture at 60° C.
  2. temperatureCool the reaction mixture
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-cfc9fddd1ffd4ca7b13fe7a2481c4b46
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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