Sodium Cyanide → HCID 24786670, compound

HRID 1042602Notes

Reaction equation

HRID 1042602 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-d9bb487a7b2d434692984d36884204da
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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