Trimethylsilyl cyanide → HCID 82623563, compound

HRID 594767Notes

Reaction equation

HRID 594767 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[Si]([C:17]#[N:18])(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1(C)C=CC=CC=1.[Zn+2].[I-].[I-]>[NH2:18][CH2:17][C:6]1([OH:12])[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:11][C:10]=2[O:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 21226445Aluminium lithium hydrideHCID 223357367-bromo-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 82623563HCID 82623563, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-bromochroman-4-one (5.00 g, 22.0 mmol) and ZnI2 (30 mg) in toluene (50 mL) was added TMSCN (4.36 g, 44.0 mmol), and the mixture was heated at 60° C. overnight. The reaction mixture was cooled to rt, and a solution of LAH (20.0 mL, 2.4 M in THF, 44.0 mmol) was added slowly. The mixture was stirred at 40° C. for 2 h. The reaction was quenched with the addition of EtOAc (10 mL) at 0° C., followed by water (5 mL) and aqueous 10% NaOH (5 mL). The reaction mixture was diluted with EtOAc, dried (MgSO4), filtered through Celite, and concentrated to give 4.5 g (79%) of the crude 4-(aminomethyl)-7-bromo-3,4-dihydro-2H-1-benzopyran-4-ol intermediate as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customThe reaction was quenched with the addition of EtOAc (10 mL) at 0° C.
  3. additionThe reaction mixture was diluted with EtOAc
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through Celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4dbdbc8ad999446fb3de45b8612f6bb3
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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