Sodium Cyanide → 2-Cyano-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran

HRID 1191992Notes

Reaction equation

HRID 1191992 reaction equation
Br[C:2]1[O:3][C:4]2[C:24]([O:25][C:26](=[O:28])[CH3:27])=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.[C-:31]#[N:32].[Na+]>CS(C)=O>[C:31]([C:2]1[O:3][C:4]2[C:24]([O:25][C:26](=[O:28])[CH3:27])=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1)#[N:32]

Participants

4

Reactant 2

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

Product 1

HCID 574219642-Cyano-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuranYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran (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 (monitored by tlc), quenched with saturated ammonium chloride solution and diluted with ethylacetate (20 mL). The organic layer was separated, dried over magnesium sulfate and the solvent distilled to afford the crude material which was purified over silica gel column (eluent—Hexane:diethyl-ether 1:1 to 0:100) to afford the desired product 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 ethylacetate (20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent 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-dd6c6b0f01b64def89048d5fb609aaa1
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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