Potassium Carbonate → Dimethyl 4-[3-(4-ethoxymethoxy-3-ethylphenyl)propyl]phthalate

HRID 970833Notes

Reaction equation

HRID 970833 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][O:12][CH2:13][CH3:14])=[C:6]([CH2:15][CH3:16])[CH:5]=1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.FC(F)(F)S(O[C:32]1[CH:33]=[C:34]([C:42]([O:44][CH3:45])=[O:43])[C:35](=[CH:40][CH:41]=1)[C:36]([O:38][CH3:39])=[O:37])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C1COCC1.CN(C=O)C.P[C-]1C=CC=C1.[C-]1(P)C=CC=C1.[Fe+2].Cl[Pd]Cl>[CH2:13]([O:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH2:3][C:41]2[CH:40]=[C:35]([C:36]([O:38][CH3:39])=[O:37])[C:34](=[CH:33][CH:32]=2)[C:42]([O:44][CH3:45])=[O:43])=[CH:5][C:6]=1[CH2:15][CH3:16])[CH3:14]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 179830474-Allyl-1-ethoxymethoxy-2-ethylbenzeneHCID 190893441,2-Dimethyl 4-(trifluoromethanesulfonyloxy)benzene-1,2-dicarboxylate

Product 1

HCID 17983048Dimethyl 4-[3-(4-ethoxymethoxy-3-ethylphenyl)propyl]phthalate

Reagents, catalysts & solvents 3

HCID 178527691HCID 178527691, compoundCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5 g (22.7 mmol) of 4-allyl-1-ethoxymethoxy-2-ethylbenzene are dissolved in 100 ml of anhydrous THF, and the medium is cooled to 0° C. 6.6 g (27 mmol) of 9-BBN are added, and the medium is brought to room temperature and then stirred for 12 hours. A solution of 7.8 g (22.6 mmol) of dimethyl 4-trifluoromethanesulphonyloxyphthalate in 100 ml of DMF is added, as well as 6.2 g (44.8 mmol) of potassium carbonate. The reaction medium is degassed with a nitrogen stream, and then 930 mg (1.1 mmol) of dichloropalladium diphosphinoferrocene are added. The medium is heated at 50° C. for 3 hours, and then poured into an ammonium chloride solution and extracted with ethyl acetate. The residue obtained after drying and concentration is purified by chromatography on a silica column (eluent heptane, and then heptane 85/ethyl acetate 15). A yellow oil is obtained (m=6.9 g, y=73%).

Workup

  1. customis brought to room temperature
  2. customThe reaction medium is degassed with a nitrogen stream
  3. temperatureThe medium is heated at 50° C. for 3 hours
  4. extractionextracted with ethyl acetate
  5. customThe residue obtained
  6. customafter drying
  7. concentrationconcentration
  8. customis purified by chromatography on a silica column (eluent heptane
  9. customA yellow oil is obtained (m=6.9 g, y=73%)

Sources & evidence

ORD record
ord-6286cf73ffb045358356c73e33984bd0
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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