Dimethyl Sulfide → Methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]phenoxy}methyl)benzoate

HRID 2112026

Reaktionsgleichung

Reaktionsgleichung von HRID 2112026
C([O:8][C:9]1[CH:36]=[CH:35][C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:34]=[CH:33][C:20]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=3[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CSC.B(F)(F)F.CCOCC.CCOC(C)=O>ClCCl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:34]=[CH:33][C:20]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=3[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)=[CH:35][CH:36]=1

Komponenten

6

Edukt 4

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 68869717Methyl 2-[(4-{3-[4-(benzyloxy)phenoxy]propyl}phenoxy)methyl]benzoate

Produkt 1

HCID 68869776Methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]phenoxy}methyl)benzoateAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 2-[(4-{3-[4(benzyloxy)phenoxy]propyl}phenoxy)methyl]benzoate (0.70 g, 1.45 mmol) was dissolved in dichloromethane (10 ml). Dimethylsulfide (1.08 g, 17.4 mmol) and borontrifluoride etherate (2.06 g, 14.5 mmol) was added and the mixture was stirred at room temperature for six hours. EtOAc (10 ml) was added and the organic phase was washed with water (3×10 ml), dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by preparative HPLC (started with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). After removing the solvent by evaporation 0.328 gram of methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]-phenoxy}methyl)benzoate (yield 57.6%) was obtained.

Aufarbeitung

  1. washthe organic phase was washed with water (3×10 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe crude was purified by preparative HPLC (
  5. concentrationthe acetonitrile concentration
  6. temperaturewas increased to 100%
  7. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min))
  8. additionThe product containing fractions
  9. customthe acetonitrile was removed by evaporation
  10. additionEtOAc (10 ml) was added
  11. washthe organic phase was washed with two portions of brine
  12. dry with materialdried (MgSO4)
  13. customAfter removing the solvent

Quellen und Nachweise

ORD-Eintrag
ord-ab7935c136134be4ab60bbeb9ec1e460
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521461B2

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