Phosphoric Acid → 2-(4-Methylsulfonylphenyl)-1-phenylazulene

HRID 1456822Notes

Reaction equation

HRID 1456822 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2C(OC)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].P(=O)(O)(O)O>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[C:13]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=[CH:14]3)[C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 1004Phosphoric AcidHCID 22107203Methyl 2-(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate

Product 1

HCID 221071632-(4-Methylsulfonylphenyl)-1-phenylazuleneYield 89.4%

Conditions

Temperature
120 °C

Procedure

Methyl 2-(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate(0.13 g) was treated with 100% phosphoric acid (5.0 ml). After stirring for 10 min at 120° C., the reaction mixture was poured into ice-water, followed by extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4 and concentrated. The crude product was purified by SiO2 column chromatography (benzenee/Et2O, 50: 1) to give the title compound (0.10 g) as violet crystals; mp 139°-140° C.

Workup

  1. extractionby extracted with EtOAc
  2. washThe combined EtOAc extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by SiO2 column chromatography (benzenee/Et2O, 50: 1)

Sources & evidence

ORD record
ord-4450231d752345ca9a88b2df2f88f361
Source dataset
uspto-grants-1998_12
Patent number
US05843999

Reaction notes

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