Dimethylformamide → HCID 15020221, compound

HRID 1090182Notes

Reaction equation

HRID 1090182 reaction equation
O=P(Cl)(Cl)Cl.[CH:6]([C:9]1[CH:18]=[C:17]2[C:13](=[C:14]([CH2:19][CH2:20][OH:21])[CH:15]=[CH:16]2)[CH:12]=[CH:11][CH:10]=1)([CH3:8])[CH3:7].[OH-].[Na+].CN([CH:27]=[O:28])C>>[CH:6]([C:9]1[CH:18]=[C:17]2[C:13](=[C:14]([CH2:19][CH2:20][OH:21])[CH:15]=[C:16]2[CH:27]=[O:28])[CH:12]=[CH:11][CH:10]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 15020220HCID 15020220, compound

Product 1

HCID 15020221HCID 15020221, compoundYield 98.1%

Procedure

A POCl3 (0.4 ml ) was added to DMF (5.0 ml ) at 0° C. and stirred for 10 min. To this mixture, 0.5 g of 7-Isopropyl-[3-(2-hydroxyethyl)]-azulene in DMF (2.5 ml) was added and stirred at 0° C. for 30 min. The mixture was poured into icewater and basified with 10% NaOH solution. The solution was extracted with ethyl acetate. The ethyl acetate extracts were washed with H2O and brine, dried (MgSO4), then concentrated to dryness. Purification of the residue by silica gel column chromatography (elution with ether) gave 0.556 g of the desired compound (98.1%)

Workup

  1. stirringstirred at 0° C. for 30 min
  2. additionThe mixture was poured into icewater
  3. extractionThe solution was extracted with ethyl acetate
  4. washThe ethyl acetate extracts were washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness
  7. customPurification of the residue
  8. washby silica gel column chromatography (elution with ether)

Sources & evidence

ORD record
ord-6ea3d888869a49629a34c01e0926cba2
Source dataset
uspto-grants-1992_01
Patent number
US05081152

Reaction notes

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