Triacetoxyperiodinane → 1-formyl-3,4-dihydro-1H-isochromene-5-carbonitrile

HRID 2173261Notes

Reaction equation

HRID 2173261 reaction equation
[OH:1][CH2:2][CH:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:7]=2[CH2:6][CH2:5][O:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:7]=2[CH2:6][CH2:5][O:4]1)=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 666465561-(hydroxymethyl)-3,4-dihydro-1H-isochromene-5-carbonitrile

Product 1

HCID 595686551-formyl-3,4-dihydro-1H-isochromene-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(hydroxymethyl)-3,4-dihydro-1H-isochromene-5-carbonitrile (0.16 g, 0.85 mmol) in 4 mL of DCM was added Dess-Martin reagent (0.72 g, 1.7 mmol) in one portion at 0° C. The mixture was stirred at 0° C. for 1 hour, and then stirred at rt. Overnight. The reaction mixture was filtered and the filtrate was concentrated to give 1-formyl-3,4-dihydro-1H-isochromene-5-carbonitrile. 1H-NMR (400 MHz, CDCl3) δ 9.71 (s, 1H), 7.93˜7.95 (in, 1H), 7.64˜7.68 (m, 1H), 4.99 (s, 1H), 4.03˜4.09 (m, 2H), 2.99˜3.04 (m, 2H).

Workup

  1. stirringstirred at rt
  2. customOvernight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-961fd2dbb3384bb5afe8d7075cded343
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…