Sodium Cyanide → HCID 10656328, compound

HRID 964814Notes

Reaction equation

HRID 964814 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+]>CS(C)=O.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

5

Reactant 2

HCID 8929Sodium CyanideHCID 10730662HCID 10730662, compound

Product 1

HCID 10656328HCID 10656328, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 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 dimethylsulfoxide (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 (hexane-isopropyl 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 (hexane-isopropyl ether, 2:1)
  6. customThe crude crystals obtained
  7. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-a97b6c3e45904ab59c461c5fdcc485ac
Source dataset
uspto-grants-1998_06
Patent number
US05770772

Reaction notes

Loading…