Ethylenediamine → (1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

HRID 2056722Notes

Reaction equation

HRID 2056722 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:14]=1.[Cu][C:16]#[N:17].C(N)CN>CN(C=O)C.[Cu]I>[OH:13][CH2:12][CH2:11][C@H:10]1[C:5]2[CH:4]=[CH:3][C:2]([C:16]#[N:17])=[CH:14][C:6]=2[CH2:7][CH2:8][O:9]1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 536878432-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanolHCID 178418546HCID 178418546, compound

Product 1

HCID 69306499(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (300 g, 1.17 mol), copper(I) cyanide (209 g, 2.34 mol), and copper(I) iodide (33.3 g, 0.18 mol) in dry DMF (1.16 L), under an atmosphere of nitrogen, was heated to 140° C. After 8 h at this temperature, HPLC analysis of an aliquot indicated that the reaction was complete. The reaction mixture was cooled to room temperature and poured into an aqueous solution of ethylenediamine (3 L, v/v 3/1) then extracted into toluene. The combined organic layers were washed with water and concentrated in vacuo to give the crude title compound. This material is used without further purification in the subsequent step.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthen extracted into toluene
  3. washThe combined organic layers were washed with water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f48a1f58210433eac5430ccd496ee52
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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