HCID 57437182, compound → HCID 57437183, compound

HRID 2064758Notes

Reaction equation

HRID 2064758 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]#[CH:13])[CH:5]=1>C(N(CC)C1C=CC=CC=1)C.CCOCC>[CH3:1][O:2][C:3]([C:4]1[C:5]2[CH:13]=[CH:12][CH2:11][O:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)=[O:14]

Participants

4

Reactant 1

HCID 57437182HCID 57437182, compound

Product 1

HCID 57437183HCID 57437183, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7061N,N-DiethylanilineSolvent

Procedure

A solution of 3-prop-2-ynyloxy-benzoic acid methyl ester (10.5 mmol) in N,N-diethylaniline (20 mL) is heated to reflux for 15 h. The mixture is cooled to RT, diluted with ether and washed with hydrochloric acid (5%) and brine. The solvents are removed in vacuo and the residue is purified by chromatography (silica, heptane to heptane/EtOAc 95/5) to give the desired chromene derivative. 1H-NMR (CDCl3): δ=3.91 (s, 3H); 4.80 (bs, 2H); 5.93-5.98 (m, 1H); 6.99 (d, J=8.03 Hz, 1H); 7.16 (t, J=7.66 Hz, 1H); 7.34 (d, J=10.3 Hz, 1H); 7.50 (d, J=7.28 Hz, 1H).

Workup

  1. temperatureto reflux for 15 h
  2. washwashed with hydrochloric acid (5%) and brine
  3. customThe solvents are removed in vacuo
  4. customthe residue is purified by chromatography (silica, heptane to heptane/EtOAc 95/5)

Sources & evidence

ORD record
ord-a66056dc8ac2477b92eaf9526acaf1e7
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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