Sodium Cyanide → HCID 10656328, compound

HRID 234276Notes

Reaction equation

HRID 234276 reaction equation
Br[CH2:2][C:3]1([CH3:15])[CH2:7][C:6]2[C:8]([CH3:14])=[CH:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[C-:16]#[N:17].[Na+]>O>[C:16]([CH2:2][C:3]1([CH3:15])[CH2:7][C:6]2[C:8]([CH3:14])=[CH:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1)#[N:17]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 10730662HCID 10730662, compound

Product 1

HCID 10656328HCID 10656328, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (6.5 g, 18.6 mmol) was dissolved in dimethylsufoxide (30 ml). Sodium cyanide (1.43 g, 88 mmol) was added and the resulting mixture was stirred at 80° C. for 18 hours. The reaction mixture was diluted with water and the product was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexaneisopropyl ether, 2:1). The crude crystals obtained were recrystallized from methanol to obtain the desired compound (4.1 g, yield: 79.7%), m.p. 58°-59° C.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexaneisopropyl ether, 2:1)
  6. customThe crude crystals obtained
  7. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-a9fcd05585e04191965113a85a6b1655
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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