Diglyme → (1S,2R,4aS,8aS)-1-(2,4-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

HRID 422145

Reaktionsgleichung

Reaktionsgleichung von HRID 422145
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].[OH:12][CH2:13][C@@H:14]1[C@:23]2([CH3:24])[C@H:18]([C:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][CH2:22]2)[CH2:17][CH2:16][C@@:15]1([CH3:28])[OH:27].C([O-])([O-])=O.[Cs+].[Cs+].COCCOCCOC>CCOC(C)=O.[Cu]I.C1(C)C=CC=CC=1>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[O:12][CH2:13][C@@H:14]1[C@:23]2([CH3:24])[C@H:18]([C:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][CH2:22]2)[CH2:17][CH2:16][C@@:15]1([CH3:28])[OH:27]

Komponenten

8

Edukt 4

HCID 8150DiglymeHCID 10796Cesium carbonateHCID 1406941-Iodo-2,4-dimethoxybenzeneHCID 10879261(1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

Produkt 1

HCID 58294797(1S,2R,4aS,8aS)-1-(2,4-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-olAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In a sealed tube purged with nitrogen, 1-iodo-2,4-dimethoxybenzene (40) (3.02 g, 11.4 mmol), (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (3) (2.50 g, 10.4 mmol), Cs2CO3 (5.10 g, 15.6 mmol), 3,4,7,8-tetramethyl-[1,10]-phenylthroline (0.50 g, 2.1 mmol), CuI (0.16 g, 1.0 mmol), diglyme (10 mL) and toluene (30 mL) were placed. The reaction mixture was stirred at 130° C. for 18 h. The reaction was cooled to room temperature, diluted with EtOAc (600 mL) and washed with water (200 mL). The solid material was removed by filtration. The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1S,2R,4aS,8aS)-1-(2,4-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (41) (2.50 g, 64%) as an off white solid.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water (200 mL)
  3. customThe solid material was removed by filtration
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (Hexanes/EtOAc, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-29009009950c4c8b84db208e850ac8ce
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101605B2

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