Isoprene → 2-Oxabicyclo[3.2.2]nonan-7-ol

HRID 1719824

Reaktionsgleichung

Reaktionsgleichung von HRID 1719824
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][O:2]2.C(C=C)=[O:11].C=CC(=C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[Mg]Br>>[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH:7]1[OH:11])[CH2:4][CH2:3][O:2]2

Komponenten

6

Edukt 5

HCID 6557IsopreneHCID 7847AcroleinHCID 11776TriphenylphosphineHCID 201980142-Oxabicyclo[3.2.2]nonaneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 201979862-Oxabicyclo[3.2.2]nonan-7-ol

Versuchsvorschrift

When m is 1, n is 2 and p is 2, the ring system is a 2-oxabicyclo[3.2.2]nonane, another subclass of this invention. For example, compound XVp ##STR29## in which R2, R5 and R6 are methyl can be prepared by treating a Diels-Alder adduct of acrolein and isoprene with Ph3P=C(CH3)OCH3, hydrolyzing the resulting enol ether, treating the resulting ketone derivative with methyl magnesium bromide, and subjecting the resulting alcohol to epoxidation-cyclization to yield a 2-oxabicyclo[3.2.2]nonan-7-ol, which is treated with WCH2X in which X is a halogen atom to yield the desired ether, XVp. Alternatively, 4-methyl-3-cyclohexene-1-acetic acid, as obtained by the method of Kugatova-Shemyakina et al., Chemical Abstracts, 65:10504c (1966) is treated with methyl Grignard followed by epoxidation-cyclization of the resulting alcohol to yield a 2-oxabicyclo[3.2.2]nonan-7-ol.

Aufarbeitung

  1. customcan be prepared

Quellen und Nachweise

ORD-Eintrag
ord-b2eb9308c9924c92b1521df84814d506
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04542244

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