Diglyme → (1S,2R,4aS,8aS)-1-(3,5-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

HRID 422142

Reaktionsgleichung

I[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.[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>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([O:10][CH3:11])[CH:5]=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

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

In a sealed tube purged with nitrogen, 1-iodo-3,5-dimethoxybenzene (36) (0.78 g, 3.0 mmol), (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (3) (0.65 g, 2.68 mmol), Cs2CO3 (1.3 g, 4.0 mmol), 3,4,7,8-tetramethyl-[1,10]-phenylthroline (0.12 g, 0.50 mmol), CuI (0.05 g, 0.3 mmol), diglyme (2 mL) and toluene (10 mL) were added. The reaction mixture was stirred at 120° C. for 18 h. The reaction was cooled to room temperature, diluted with EtOAc (300 mL) and washed with water (100 mL). The organic layer was dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 2:1) gave (1S,2R,4aS,8aS)-1-(3,5-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (37) (0.71 g, 70%) as a colourless oil.

Aufarbeitung

additionwere added
temperatureThe reaction was cooled to room temperature
washwashed with water (100 mL)
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated
customPurification by column chromatography on silica gel (Hexanes/EtOAc, 2:1)

Quellen und Nachweise

ORD-Eintrag: ord-17c99bf7cc9046eb816ff65e957a6ff5
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101605B2

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