Benzo(b)naphtho(2,3-d)furan → HCID 14770208, compound

HRID 1710155Notes

Reaction equation

HRID 1710155 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[C:11]4[C:16](=[CH:17][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:15]=[CH:14][CH:13]=[CH:12]4.C1C2C3=CC4C(C(C=O)=C3[O:23][C:22]=2C=CC=1)=CC=CC=4>C1(C)C=CC=CC=1.CCCCCC>[CH:1]1[C:9]2[C:8]3[C:10]([CH:22]=[O:23])=[C:11]4[C:16](=[CH:17][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:15]=[CH:14][CH:13]=[CH:12]4

Participants

4

Reactant 2

HCID 71072Benzo(b)naphtho(2,3-d)furanHCID 14555909HCID 14555909, compound2×

Product 1

HCID 14770208HCID 14770208, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21889329Toluene hexaneSolvent

Procedure

Benzo[b]naphtho[2,3-d]furan (H. G. Pars Pharmaceutical Laboratories, Inc.) was formylated using the procedure of A. Rieche et al., Chem. Ber. 93, 88 (1960). The crude aldehyde appeared to be mainly one isomer accompanied by a small amount of a second aldehyde by TLC. Purification by chromatography (SiO2, PhCH3) followed by recrystallization (CH2Cl2 /hexane) gave the main component in 58% yield identified using NMR techniques to be benzo[b]naphtho[2,3-d]furan-6-carbaldehyde, (2A) mp 169°-171.5°, (C,H). The minor component, obtained in 3.4% yield was shown by NMR to be benzo[b]naphtho2,3-d]-furan-11-carbaldehyde, mp 128°-132°, (C,H), (PhCH3 /hexane).

Workup

  1. customPurification by chromatography (SiO2, PhCH3)
  2. customfollowed by recrystallization (CH2Cl2 /hexane)
  3. customgave the main component in 58% yield
  4. customThe minor component, obtained in 3.4% yield

Sources & evidence

ORD record
ord-d99c9d6f7ed740f2b77a543a4f687c42
Source dataset
uspto-grants-1990_08
Patent number
US04952597

Reaction notes

Loading…