Toluene → alpha-Cyano-3-phenoxybenzyl (1R,trans)-2,2-dimethyl-3-((cyclopropylmethoxyimino)methyl)cyclopropanecarboxylate

HRID 127016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 127016
[CH3:1][C:2]1([CH3:15])[C@H:4]([CH:5]=[N:6][O:7][CH2:8][CH:9]2[CH2:11][CH2:10]2)[C@H:3]1[C:12]([OH:14])=[O:13].[C:16]([CH:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)#[N:17].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:1][C:2]1([CH3:15])[C@H:4]([CH:5]=[N:6][O:7][CH2:8][CH:9]2[CH2:10][CH2:11]2)[C@H:3]1[C:12]([O:14][CH:18]([C:16]#[N:17])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:20]=1)=[O:13]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 12713810alpha-Cyano-3-phenoxybenzyl bromideHCID 53706710(1R,trans)-2,2-dimethyl-3-((cyclopropylmethoxyimino)methyl)cyclopropanecarboxylic acid

Produkt 1

HCID 86737089alpha-Cyano-3-phenoxybenzyl (1R,trans)-2,2-dimethyl-3-((cyclopropylmethoxyimino)methyl)cyclopropanecarboxylateAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1.8 g of (1R,trans)-2,2-dimethyl-3-((cyclopropylmethoxyimino)methyl)cyclopropanecarboxylic acid, 2.30 g of α-cyano-3-phenoxybenzyl bromide, 0.05 g of tetrabutylammonium hydrogen sulfate, 0.05 g of benzyltriethylammonium chloride, 0.58 g of potassium carbonate, 10 ml of toluene and 6 ml of water was heated at 60°-70° for 4 hours, let stand overnight at room temperature and reheated at 60°-70° for an additional eight hours. The resulting reaction mixture separated into layers. The toluene layer was separated, washed with water, then with saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate and stripped to give an oil. This oil was chromatographed on silica gel with a mixture of ether-pentane (1:4 ratio) as the eluant to give 2.7 g of desired product as a yellow oil, [α]D25 -16.2, (CHCl3 ; c=0.02 g/cc).

Aufarbeitung

  1. temperaturewas heated at 60°-70° for 4 hours
  2. waitreheated at 60°-70° for an additional eight hours
  3. customThe resulting reaction mixture
  4. customseparated into layers
  5. customThe toluene layer was separated
  6. washwashed with water
  7. dry with materialwith saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate
  8. customto give an oil
  9. customThis oil was chromatographed on silica gel with a mixture of ether-pentane (1:4 ratio) as the eluant

Quellen und Nachweise

ORD-Eintrag
ord-0b64c4aa82874efa87ae78aef68c0a86
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254277

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