Dimethylformamide → HCID 18182573, compound

HRID 1359594Notes

Reaction equation

HRID 1359594 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[C:8]2[CH:9]=[C:10](Br)[CH:11]=[CH:12][C:7]=2[O:6][CH2:5]1.[CH3:14][N:15](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:1][CH2:2][CH2:3][CH:4]1[C:8]2[CH:9]=[C:10]([C:14]#[N:15])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5]1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 18182599HCID 18182599, compound

Product 1

HCID 18182573HCID 18182573, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of zinc cyanide (1.97 g, 17 mmol) and (Ph3P)4Pd (498 mg, 0.4 mmol) is added 3-(2-hydroxy-ethyl)-5-bromo-2,3-dihydro-benzofuran (reference example 14, 1.1 g, 4.3 mmol) in DMF (12 mL). The resulting mixture is heated to 75° C. and stirred at this temperature for 14 hr. The reaction mixture is then allowed to cool then diluted with ethyl acetate, washed with 5% aq. ammonia solution then brine. The organic phase is dried over Mg SO4 then concentrated. The residue is purified by flash chromatography (50% ethyl acetate in hexanes) to give the product (653 mg) as a white solid.

Workup

  1. temperatureto cool
  2. washwashed with 5% aq. ammonia solution
  3. dry with materialThe organic phase is dried over Mg SO4
  4. concentrationthen concentrated
  5. customThe residue is purified by flash chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8f6dea101f13482a8697f968d20b8da5
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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