Water → 2-(1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)ethanol

HRID 1047466Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[CH:6]2[O:11][CH3:12].[Li]CCCC.[CH2:19]1[O:21][CH2:20]1.O>C1COCC1>[CH3:12][O:11][CH:6]1[C:7]2[C:3](=[C:2]([CH2:19][CH2:20][OH:21])[CH:10]=[CH:9][CH:8]=2)[CH2:4][CH:5]1[CH3:13]

Participants

Conditions

Temperature: -110 °C

Procedure

To a solution of 20.0 g (82.9 mmol) of 4-bromo-2-methyl-methoxyindane in 200 ml of THF 33.2 ml of 2.5 M (83.0 mmol) n-BuLi in hexanes was added for 20 min at −80° C. This mixture was stirred for 40 min at this temperature, cooled to −110° C., and 4.38 g (99.4 mmol) of ethylene oxide was added by one portion at vigorous stirring. The resulting mixture was stirred for 12 h at room temperature, and then 10 ml of water was added. The organic layer was separated and evaporated to dryness. To the residue 200 ml of water was added, and the crude product was extracted with 3×100 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography using short column with Silica Gel 60 (40-63 um, d 110 mm, 190 mm; eluent: hexanes/ether=20/1). Yield 12.7 g (74%) of a ca. 1 to 1.2 mixture of two diastereomers.

Workup

stirringThe resulting mixture was stirred for 12 h at room temperature
customThe organic layer was separated
customevaporated to dryness
additionTo the residue 200 ml of water was added
extractionthe crude product was extracted with 3×100 ml of dichloromethane
extractionThe combined organic extract
dry with materialwas dried over Na2SO4
customevaporated to dryness
customThe product was isolated by flash chromatography
additionYield 12.7 g (74%) of a ca. 1 to 1.2 mixture of two diastereomers

Sources & evidence

ORD record: ord-4752fe46a52443be9a78d3a625278808
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569532B2

Reaction notes

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