Water → 4-(9H-fluoren-9-ylmethyl)-2-methyl-2,3-dihydro-1H-inden-1-yl methyl ether

HRID 1047469Notes

Reaction equation

[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li]CCCC.Br[CH2:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH2:23][CH:24]([CH3:32])[CH:25]2[O:30][CH3:31].O>CCOCC>[CH3:31][O:30][CH:25]1[C:26]2[C:22](=[C:21]([CH2:20][CH:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[CH:29]=[CH:28][CH:27]=2)[CH2:23][CH:24]1[CH3:32]

Participants

Conditions

Temperature: -80 °C

Procedure

To a solution of 3.32 g (0.20 mol) of 9H-fluorene in 500 ml of ether 80 ml of 2.5 M (0.20 mol) n-BuLi in hexanes was added at 0° C. This mixture was stirred for 12 h, cooled to −80° C., and then a solution of 5.10 g (0.20 mol) of 4-(bromomethyl)-1-methoxy-2-methylindane in 150 ml of ether was added dropwise by vigorous stirring for 30 min at this temperature. The resulting mixture was stirred for 24 h at room temperature, and then 500 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 3×200 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 60 mm, l 150 mm; eluent: hexanes/ether=20/1). Yield 5.31 g (78%) of a mixture of the diastereomers A and B.

Workup

stirringby vigorous stirring for 30 min at this temperature
stirringThe resulting mixture was stirred for 24 h at room temperature
customThe organic layer was separated
extractionthe aqueous layer was extracted with 3×200 ml of dichloromethane
extractionThe combined organic extract
dry with materialwas dried over Na2SO4
customevaporated to dryness
customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 60 mm, l 150 mm; eluent: hexanes/ether=20/1)

Sources & evidence

ORD record: ord-8c23549ceb6e476690ddeafe9cd4356b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569532B2

Reaction notes

Loading…