Water → 1-(2-Cyanoethyl)-6-methoxyindan

HRID 1977997

Reaction equation

Br[CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5]1.[C-:15]#[N:16].[Na+].O>CS(C)=O>[C:15]([CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5]1)#[N:16]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-bromoethyl)-6-methoxyindan (1.75 g, 6.86 mmol) in dimethyl sulfoxide (80 ml) was added sodium cyanide (0.35 g, 7.20 mmol). This mixture was stirred for 40 minutes at 60° C. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with brine and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane/ethyl acetate, 85:15) to give 1.28 g (yield 93%) of the above-titled compound as an oily-product.

Workup

extractionwas subjected to extraction with ethyl acetate
washThe extract solution was washed with brine
dry with materialdried over anhydrous magnesium sulfate
distillationby distilling off the solvent under reduced pressure
customThe residue was purified by means of a silica gel column chromatography (hexane/ethyl acetate, 85:15)

Sources & evidence

ORD record: ord-0b31ccfc063a4c8fa74faea8605d7839
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235789B1

Linked notes

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