Methyl 4-(chloromethyl)benzoate → Methyl 8-(2-benzyloxyphenyl)-6-(4-methoxycarbonylbenzyl)-7-octenoate

HRID 983648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 983648
[Br-].[CH2:2]([O:9][C:10]1[CH:35]=[CH:34][CH:33]=[CH:32][C:11]=1[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[CH:41]([CH:43]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]([O:61][CH3:62])=[O:60])=[CH:55][CH:54]=1)[CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50][CH3:51])=[O:49])=O.O=C1CCCCC1C(OC(C)(C)C)=O.ClCC1C=CC(C(OC)=O)=CC=1>C1COCC1.O>[CH2:2]([O:9][C:10]1[CH:35]=[CH:34][CH:33]=[CH:32][C:11]=1[CH:12]=[CH:41][CH:43]([CH2:52][C:53]1[CH:54]=[CH:55][C:56]([C:59]([O:61][CH3:62])=[O:60])=[CH:57][CH:58]=1)[CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50][CH3:51])=[O:49])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

8

Edukt 5

HCID 36664Methyl 4-(chloromethyl)benzoateHCID 11255212Methyl 6-formyl-7-(4-methoxycarbonylphenyl)heptanoateHCID 114101092-(Benzyloxy)benzyl-triphenylphosphonium bromideHCID 12431017tert-Butyl 2-oxocyclohexane-1-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 69632062Methyl 8-(2-benzyloxyphenyl)-6-(4-methoxycarbonylbenzyl)-7-octenoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

At 0° C. and under argon, 343.4 mg (0.64 mmol) of 2-(benzyloxy)benzyl-triphenylphosphonium bromide from Ex. III are suspended in 20 ml of THF, and 0.48 ml of butyllithium (0.76 mmol, 1.6 M solution in hexane) is added. The deep-orange solution is stirred at 0° C. for 30 min, and a solution of 195 mg (0.64 mmol) of methyl 6-formyl-7-(4-methoxycarbonylphenyl)heptanoate (prepared analogously to Example I from t-butyl 2-oxocyclohexanecarboxylate and methyl 4-chloromethylbenzoate, cf. EP-A-0 341 551) in 15 ml of THF is added dropwise at this temperature. The mixture is stirred at 0° C. for 30 min. At 0° C., water is added, and the mixture is then warmed to room temperature and extracted with ethyl acetate. The organic phase is washed with sodium chloride solution, dried with magnesium sulfate and concentrated using a rotary evaporator. For purification, the substance was chromatographed on 40 g of silica gel 60 (particle size 0.040-0.063 mm) using the mobile phase petroleum ether/ether 4:1 to 1:1.

Aufarbeitung

  1. customAt 0° C.
  2. stirringThe mixture is stirred at 0° C. for 30 min
  3. temperaturethe mixture is then warmed to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customa rotary evaporator
  9. customFor purification
  10. customthe substance was chromatographed on 40 g of silica gel 60 (particle size 0.040-0.063 mm)

Quellen und Nachweise

ORD-Eintrag
ord-ec7e86931cb44f2ca4292f6bcafd406c
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06864287B1

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