Propionyl chloride → HCID 58309307, compound

HRID 537636Notes

Reaction equation

HRID 537636 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)[O:14][C:13]3[C:15]4[C:20]([C:21]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[C:22]([C:23]([O:25][CH2:26][CH2:27][OH:28])=[O:24])[C:12]=3[CH:11]=[CH:10]2)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:5][CH:4]=1.[C:43](Cl)(=[O:46])[CH2:44][CH3:45]>ClCCl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:35]3[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=3)[O:14][C:13]3[C:15]4[C:20]([C:21]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)=[C:22]([C:23]([O:25][CH2:26][CH2:27][O:28][C:43](=[O:46])[CH2:44][CH3:45])=[O:24])[C:12]=3[CH:11]=[CH:10]2)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 62324Propionyl chlorideHCID 23298978HCID 23298978, compound

Product 1

HCID 58309307HCID 58309307, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2,2-Bis(4-methoxyphenyl)-5-(2-hydroxyethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran (U.S. Pat. No. 6,113,814) (0.50 g, 0.90 mmol) was dissolved in dry dichloromethane (20 ml) together with triethylamine (0.25 ml), under nitrogen. To this solution was added propionyl chloride (0.083 g, 0.90 mmol) and the mixture stirred at RT for 15 minutes. The solvent was evaporated and the crude residue purified by column chromatography (silica gel, EtOAc/hexane, 2:3) giving a pink foamy solid on evaporation of the solvent in vacuo. Analysis of the purified product by 1H NMR gave a spectrum consistent with the structure of 2,2-Bis(4-methoxyphenyl)-5-(2-propionyloxy-ethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran.

Workup

  1. customThe solvent was evaporated
  2. customthe crude residue purified by column chromatography (silica gel, EtOAc/hexane, 2:3)
  3. customgiving a pink foamy solid
  4. customon evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-84e03cb172824aa68911009395f6b5f1
Source dataset
uspto-grants-2014_10
Patent number
US08865029B2

Reaction notes

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