Diazomethane → Methyl 7-[2-methoxy-5-(3-methoxy-1-octenyl)cyclopentyl]heptanoate

HRID 1581114

Reaktionsgleichung

Reaktionsgleichung von HRID 1581114
OC1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].[N+](=[CH2:28])=[N-].[B-](F)(F)(F)[O+:30]([CH3:32])[CH3:31]>C(OCC)C>[CH3:31][O:30][CH:32]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([O:15][CH3:28])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23]

Komponenten

5

Edukt 3

HCID 9550Diazomethane2×HCID 54187079Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoateHCID 178494437HCID 178494437, Verbindung

Produkt 1

HCID 54112136Methyl 7-[2-methoxy-5-(3-methoxy-1-octenyl)cyclopentyl]heptanoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

A solution of methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (0.6 g.) [prepared as described in Example 5] in dry diethyl ether (30 ml.) was cooled to -40°C. Freshly prepared dry diazomethane in diethyl ether, cooled to -40°C., was added to the solution of methyl ester immediately after the addition of boron trifluoride dimethyl etherate (3 ml.). Diazomethane solution was added until the yellow colour persisted. After 15 minutes at -40°C. and standing at ambient temperature overnight the solution was filtered from precipitated polymethylenes, washed with sodium bicarbonate solution and water, dried over anhydrous sodium sulphate and evaporated in vacuo. The last traces of solvent were removed by pumping under high vacuum to give methyl 7-[2-methoxy-5-(3-methoxy-1-octenyl)cyclopentyl]heptanoate (0.42 g., 65%). (Found: C, 72.4; H, 10.3. C23H42O4 requires C, 72.3; H,11.0%) νmax 1730 cm-1, 1100 cm-1 and 990 cm-1 (liquid film).

Aufarbeitung

  1. waitstanding at ambient temperature overnight
  2. filtrationthe solution was filtered
  3. customfrom precipitated polymethylenes
  4. washwashed with sodium bicarbonate solution and water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated in vacuo
  7. customThe last traces of solvent were removed

Quellen und Nachweise

ORD-Eintrag
ord-684100cd70f9448aa516bdda328325d2
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03935261

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