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Ammonium Chloride → (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethylhexadecan-3-ol

HRID 1200276
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1200276
[CH3:1][C@H:2]([CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:3][CH2:4]Br.[Mg].[CH3:18][O:19][C:20]1[C:25]([CH3:26])=[C:24]([CH3:27])[C:23]([O:28][CH3:29])=[C:22]([CH3:30])[C:21]=1[CH2:31][CH2:32][C@:33]1([CH3:36])[O:35][CH2:34]1.[Cl-].[NH4+]>C(OCC)(=O)C>[CH3:18][O:19][C:20]1[C:25]([CH3:26])=[C:24]([CH3:27])[C:23]([O:28][CH3:29])=[C:22]([CH3:30])[C:21]=1[CH2:31][CH2:32][C@:33]([CH3:36])([OH:35])[CH2:34][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14]
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Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 13191851(3R,7R)-1-bromo-3,7,11-trimethyldodecaneHCID 18602184(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butane

Produkt 1

HCID 14631375(3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethylhexadecan-3-ol

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5.8 mmol of (3R,7R)-3,7,11-trimethyldodecyl bromide are heated at reflux for 1/4 hour in 20 ml of ethyl acetate with activated magnesium. Then, there are added at 0° C. 1 g of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxybutane and 0.9 g of copper(I)-2-propylacetylide [or 1.2 g of copper(I) bromide/dimethyl sulphide complex]. The temperature of the reaction mixture is subsequently left to rise to room temperature and the mixture is stirred overnight. 10 ml of ammonium chloride are then added and the mixture is extracted with ethyl ether. The extract is dried and concentrated, and the residue is distilled in a bulb-tube (b.p.0.01 =140° C.). There are obtained 1.28 g (72%) [or 1.41 g (79%)] of (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethylhexadecan-3-ol as a colourless oil.

Aufarbeitung

  1. additionThen, there are added at 0° C
  2. waitThe temperature of the reaction mixture is subsequently left
  3. customto rise to room temperature
  4. extractionthe mixture is extracted with ethyl ether
  5. customThe extract is dried
  6. concentrationconcentrated
  7. distillationthe residue is distilled in a bulb-tube (b.p.0.01 =140° C.)

Quellen und Nachweise

ORD-Eintrag
ord-fdf428bfbfec4391bd8c459c4803e3c5
Quelldatensatz
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04904823

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