Dimethylformamide → 3-Benzyl-5,7-bis(cyanomethoxy)-4-methyl-2h-1-benzopyran-2-one

HRID 1862508Notes

Reaction equation

Cl[CH2:2][C:3]#[N:4].[C:5](=[O:8])([O-])[O-:6].[K+].[K+].[CH2:11]([C:18]1[C:19](=O)[O:20][C:21]2[CH:28]=[C:27]([OH:29])[CH:26]=[C:25](O)[C:22]=2[C:23]=1[CH3:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:32][N:33](C=O)C>>[CH2:11]([C:18]1[C:5](=[O:8])[O:6][C:25]2[CH:26]=[C:27]([O:29][CH2:2][C:3]#[N:4])[CH:28]=[C:21]([O:20][CH2:19][C:32]#[N:33])[C:22]=2[C:23]=1[CH3:24])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7856Chloroacetonitrile

HCID 11430Potassium Carbonate

HCID 54285313-benzyl-5,7-dihydroxy-4-methyl-2H-chromen-2-one

Product 1

HCID 154276623-Benzyl-5,7-bis(cyanomethoxy)-4-methyl-2h-1-benzopyran-2-one

Procedure

Chloracetonitrile (6.86 g), potassium carbonate (23.9 g) and 12.2 g of the product from example 1 a were stirred in 120 ml of DMF at 100° C. under nitrogen for two hours. The reaction mixture was cooled and poured into ice water. The solids were filtered and washed with water. Yield 13.8 g (88%). Melting point 147-154° C.

Workup

temperatureThe reaction mixture was cooled
filtrationThe solids were filtered
washwashed with water

Sources & evidence

ORD record: ord-721ba934622b44ca84ee457cd0597801
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06538022B1

Reaction notes

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