Sodium Cyanide → HCID 12561495, compound

HRID 1449297Notes

Reaction equation

HRID 1449297 reaction equation
Cl[CH2:2][C:3]1[C:4](=[O:17])[C:5]2[CH2:12][O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:6]=2[O:7][CH:8]=1.[C-:18]#[N:19].[Na+]>O1CCCC1.O>[CH3:2][C:3]1[C:4](=[O:17])[C:5]2[CH2:12][O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:6]=2[O:7][C:8]=1[C:18]#[N:19]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 12561493HCID 12561493, compound

Product 1

HCID 12561495HCID 12561495, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-chloromethyl-4H,5H-[1]benzopyrano[4,3-b]pyran-4-one (2.65 g, 10.65 mmoles, described in Example 5) in tetrahydrofuran (130 ml) is combined with a solution of sodium cyanide (5.3 g) in water (27 ml). The mixture is stirred overnight at room temperature and poured into water. The solution is extracted with chloroform. The chloroform extract is dried and evaporated. The residue is chromatographed on silica gel using ethyl acetate-benzene (1:19), the eluates are evaporated, and the residue is crystallized from chloroform-diethyl ether to give the title compound (0.767 g), mp 179°-181° C.; nmr (CDCl3) δ 2.25(s, 3H), 5.2(s, 2H), and 6.8-7.7(m, 4H).

Workup

  1. extractionThe solution is extracted with chloroform
  2. extractionThe chloroform extract
  3. customis dried
  4. customevaporated
  5. customThe residue is chromatographed on silica gel
  6. customthe eluates are evaporated
  7. customthe residue is crystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-f8c889419d4148deb19afb72a7d94bcb
Source dataset
uspto-grants-1980_02
Patent number
US04189490

Reaction notes

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