Sodium Thiosulfate → [4-(2-Pyrimidinyl)phenyl]-2-propynal

HRID 2416543Notes

Reaction equation

HRID 2416543 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH2:37][OH:38])=[CH:31][CH:30]=1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCl>[N:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH:37]=[O:38])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 226311353-[4-(2-Pyrimidinyl)phenyl]-2-propyn-1-ol

Product 1

HCID 22630855[4-(2-Pyrimidinyl)phenyl]-2-propynalYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the Dess-Martin reagent (1.59 g, 3.75 mmol) and 3-[4-(2-pyrimidinyl)phenyl]-2-propyn-1-ol (525 mg, 2.50 mmol, prepared as described in Reference Example 239) in dichloromethane (15 mL) was stirred at room temperature for 30 min. Aqueous 10% Na2S2O3 (25 mL) and aq. sat. NaHCO3 (15 mL) were added, the mixture was stirred for 5 min, the layers were separated, and the aqueous layer was extracted with dichloromethane (10 mL). The combined organic layers were dried (MgSO4) and concentrated to provide 465 mg (89%) of the title compound as a yellow solid. MS 209 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 5 min
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (10 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e1ee9ea0a3c44a5399c1af8e67481c1e
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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