Ethyl Acetate → HCID 22170989, compound

HRID 2376221Notes

Reaction equation

HRID 2376221 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22][OH:23])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].CCOC(C)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=[C:11]([CH:22]=[O:23])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 22171056[5-(3,4-Dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]methanol

Product 1

HCID 22170989HCID 22170989, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of [5-(3,4-dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-methanol (Example 1 Step C, 1.0 g, 2.9 mmol) in CH2Cl2 (13 mL) under N2 was added Dess-Martin periodinane (2.1 g, 4.9 mmol) at rt. After 3 h, Na2S2O3 (5.0 g, 20 mmol) dissolved in saturated NaHCO3 (25 mL) and EtOAc (25 mL) were added, and the mixture was stirred until the layers were clear. The layers were separated, and the aqueous phase was extracted with EtOAc (3×15 mL). The combined organic extracts were dried over Na2SO4 and filtered, and the solvent was removed under reduced pressure to afford 0.95 g (96%) of the crude aldehyde, which was used without further purification. HPLC: Rt=10.3 (Method A). 1H NMR (400 MHz, CDCl3): 9.98 (s, 1H), 7.32 (s, 1H), 7.30 (d, J=2.3 Hz, 1H), 7.19-7.16 (m, 2H), 6.95 (s, 1H), 6.91 (dd, J=8.1, 2.3 Hz, 1H), 6.88-6.84 (m, 2H), 3.78 (s, 3H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (3×15 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ecd85939e3f44455ac1069044f085350
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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