Methanol → 2-Cyano-2-methyl-7-methoxybenzo[1,4]benzodioxine

HRID 1866211Notes

Reaction equation

HRID 1866211 reaction equation
B(F)(F)F.C[CH2:6][O:7][CH2:8][CH3:9].C([C@@:12]1([C:21]([O:23][CH3:24])=O)[CH2:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13]1)C.C[Si]([C:29]#[N:30])(C)C.[CH3:31]O>O>[C:29]([C:8]1([CH3:9])[O:7][C:6]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:14]([O:13][CH3:31])[C:15]=3[CH:16]=[CH:12][C:21]=2[O:23][CH2:24]1)#[N:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 82115Trimethylsilyl cyanideHCID 57358441Methyl (2s)-2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylate

Product 1

HCID 686197232-Cyano-2-methyl-7-methoxybenzo[1,4]benzodioxineYield 74.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoroboron etherate (mL, 9.6 mmol) was added to a solution of the product from Step 4 (1.0 g, 4.8 mmol), trimethylsilyl cyanide (2.5 mL, 9.6 mmol) in dichlorormethane (25 mL) cooled in a ice bath. The reaction was kept at 0 C for 1 h and warmed to 25 C over 30 min. Methanol (2.0 mL) was added, followed by addition of water (50 mL). After phase separation and extraction, the crude product was purified by chromatography on silica gel to give 0.73 g (74.8% yield) of the title compound.

Workup

  1. temperaturecooled in a ice bath
  2. temperaturewarmed to 25 C over 30 min
  3. customAfter phase separation and extraction
  4. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d725b5b681cc4af7b54f3d28125fe814
Source dataset
uspto-grants-2009_12
Patent number
US07629372B2

Reaction notes

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