Sodium Cyanide → HCID 24786670, compound

HRID 2059637Notes

Reaction equation

HRID 2059637 reaction equation
Br[C:2]1[O:6][C:5]2[C:7]([O:13]C(=O)C)=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=2[C:3]=1[C:17](=[O:30])[C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=1.[C-:31]#[N:32].[Na+]>CS(C)=O>[C:31]([C:2]1[O:6][C:5]2[C:7]([OH:13])=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=2[C:3]=1[C:17](=[O:30])[C:18]1[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=1)#[N:32]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Product 1

HCID 24786670HCID 24786670, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzo[b]furan (25 mg, 0.05 mmol) and sodium cyanide (15 mg, 0.38 mmol) in dry DMSO (1 mL) under nitrogen at room temperature was stirred for 3.5 hours (tlc), quenched with saturated ammonium chloride solution and diluted with ethyl acetate (20 mL). The organic layer was separated, dried over magnesium sulfate and solvent was distilled to afford the crude material which was purified over silica gel column (eluent-Hexane: diethyl-ether 1:1 to 0:100) to afford 2-cyano-7-hydroxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzo[b]furan as pale cream solid; (13 mg, 65%); 1H NMR (300 MHz, CDCl3) δ: 7.29(d, 1H, J=8.71 Hz), 7.19(s, 2H, benzoyl Hs), 6.06(d, 1H, J=8.77 Hz), 5.82(b, 1H, OH), 3.99(s, 3H, OMe), 3.96(s, 3H, OMe), 3.88(s, 6H, 2×OMe).

Workup

  1. customquenched with saturated ammonium chloride solution
  2. additiondiluted with ethyl acetate (20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate and solvent
  5. distillationwas distilled
  6. customto afford the crude material which
  7. customwas purified over silica gel column (eluent-Hexane: diethyl-ether 1:1 to 0:100)

Sources & evidence

ORD record
ord-82c2b05621fe43768c9c082cc26c3142
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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