Tetrahydrofuran → 4-(2-Bromoethyl)-1-methoxy-2-methylindane
Reaction equation
[CH3:1][O:2][CH:3]1[C:11]2[C:6](=[C:7]([CH2:12][CH2:13]O)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[CH3:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.C1C(=O)N([Br:47])C(=O)C1>>[Br:47][CH2:13][CH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH2:5][CH:4]([CH3:15])[CH:3]2[O:2][CH3:1]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 41.3 g (0.2 mol) of 2-(1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)ethanol and 52.5 g (0.2 mol) PPh3 in 800 ml of THF 35.6 g (0.2 mol) of NBS was added at vigorous stirring for 5 min at 0° C. This mixture was stirred for 2 h at room temperature and then evaporated to dryness. A solution of the residue in 500 ml of hexanes was filtered through glass frit (G3), and the precipitate was additionally washed by 3×300 ml hexanes. The combined organic extract was evaporated to dryness. The product was isolated from the residue using flash chromatography on Silica Gel 60 (40-63 um, d 80 mm, l 250 mm; eluent: hexanes/ether=20/1, vol.). Yield 39.3 g (73%) of ca. 1 to 1 mixture of the diastereomers A and B.
Workup
- additionwas added
- stirringThis mixture was stirred for 2 h at room temperature
- customevaporated to dryness
- filtrationA solution of the residue in 500 ml of hexanes was filtered through glass frit (G3)
- washthe precipitate was additionally washed by 3×300 ml hexanes
- extractionThe combined organic extract
- customwas evaporated to dryness
- customThe product was isolated from the residue
- additionYield 39.3 g (73%) of ca. 1 to 1 mixture of the diastereomers A and B
Sources & evidence
- ORD record
- ord-f773d418e8e14874b0cb42e7709fcd4c
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569532B2
Reaction notes
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