Sodium Cyanide → Chroman-3-yl-acetonitrile

HRID 984123Notes

Reaction equation

HRID 984123 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([CH2:11]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:2]1.[C-:23]#[N:24].[Na+]>CN(C=O)C>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([CH2:11][C:23]#[N:24])[CH2:2]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 11267124Toluene-4-sulfonic acid Chroman-3-ylmethyl ester

Product 1

HCID 14838407Chroman-3-yl-acetonitrileYield 126.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 18B (1.25 g), NaCN (0.15 g) in 25 mL of DMF, were heated to 60° C. for 12 h. The solvent was removed, the reaction mixture was mixed with water (125 mL) and ether (125 mL). The ether layer was separated, washed with water, brine, dried (MgSO4), concentrated to afford compound 18C (0.67 g). mp 54-55.5° C.; MS: 174 (M+1)+. Preparation of 3-Cyanomethyl-chroman-6-sulfonyl chloride (Compound 18D)

Workup

  1. customThe solvent was removed
  2. additionthe reaction mixture was mixed with water (125 mL) and ether (125 mL)
  3. customThe ether layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b46e117ef1f645828dbbb57f7129736b
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

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