Water → HCID 18787505, compound

HRID 1107517Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[O:10][C:11]2[C:18]([CH:19]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[C:20](OCC)=[O:21])=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]=1[CH3:14])[CH3:8].O.[OH-].[Na+]>O1CCCC1>[CH2:7]([C:9]1[O:10][C:11]2[C:18]([CH:19]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH2:20][OH:21])=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]=1[CH3:14])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

300 mg (7.87 mmol) of lithium aluminium hydride and 10 ml of anhydrous tetrahydrofuran are introduced into a 100 ml round-bottomed flask. This suspension is cooled to 0° C. by an ice bath and a solution of 1 g (3.15 mmol) of ethyl 2-(2-ethyl-3-methylbenzofuran-7-yl)-2-(diethylamino)acetate in 20 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred for 1 hour at room temperature and then hydrolysed by the successive addition of 0.3 ml of water, 0.3 ml of a 15% sodium hydroxide solution and 0.9 ml of water. A white precipitate is formed which is filtered off and washed with 50 ml of ether. The filtrate is washed with 50 ml of water, dried over magnesium sulphate and concentrated under vacuum. The residue is purified by chromatography on a silica column (elution solvent: 2% methanol in dichloromethane). 0.83 g (Yield: 96%) of 2-ethyl-3-methyl-7-(1-diethylamino-2-hydroxyethyl)benzofuran is obtained in the form of a yellow oil.

Workup

customA white precipitate is formed which
filtrationis filtered off
washwashed with 50 ml of ether
washThe filtrate is washed with 50 ml of water
dry with materialdried over magnesium sulphate
concentrationconcentrated under vacuum
customThe residue is purified by chromatography on a silica column (elution solvent: 2% methanol in dichloromethane)

Sources & evidence

ORD record: ord-d45db10b5cbf4476864c2ccb9af34958
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06060508

Reaction notes

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