Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaR)- → HCID 13105999, Verbindung

HRID 1995153

Reaktionsgleichung

Reaktionsgleichung von HRID 1995153
[CH3:1][C:2]1([CH3:14])[CH:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH3:10])=[O:8])[CH:3]1[C:11]([OH:13])=[O:12].COC(/C=C\C1(C(O)=O)CC1)=O.[C:27]([C@H:29](O)[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:31]=1)#[N:28]>>[CH3:1][C:2]1([CH3:14])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH3:10])=[O:8])[C@H:3]1[C:11]([O:13][C@@H:29]([C:27]#[N:28])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:31]=1)=[O:12]

Komponenten

4

Edukt 3

HCID 156232Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaR)-HCID 54557330HCID 54557330, VerbindungHCID 131713081[Z-2-(methoxycarbonyl)-ethenyl]-cyclopropane carboxylic acid

Produkt 1

HCID 13105999HCID 13105999, Verbindung

Versuchsvorschrift

Using the procedure of Step D of Example 1, 1.5 g of (1R, cis) 2,2-dimethyl-3-([Z-2-(methoxycarbonyl)-ethenyl]-cyclopropane carboxylic acid and 1.9 g of (R)α-cyano-3-phenoxybenzyl alcohol were reacted to obtain 4.3 g of raw product. The latter was chromatographed over silica gel and was eluted with a 9-1 cyclohexane-ethyl acetate mixture to obtain 2.5 g of (R)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(methoxycarbonyl)-ethenyl]-cyclopropane carboxylate with a specific rotation of [α]D20 =+23.5°±2.5° (c=0.5% in benzene).

Aufarbeitung

  1. customwere reacted
  2. customto obtain 4.3 g of raw product
  3. customThe latter was chromatographed over silica gel
  4. washwas eluted with a 9-1 cyclohexane-ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-f639dc4048f44a5d88fc41ce91814ba8
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04402972

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