Water → HCID 57750122, compound

HRID 504603Notes

Reaction equation

HRID 504603 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[O:11]1[CH2:16][CH2:15][CH:14]([CH2:17]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:17][CH:14]2[CH2:15][CH2:16][O:11][CH2:12][CH2:13]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 19077576(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 57750122HCID 57750122, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5-chlorosalicylaldehyde (5.0 g, 32 mmol), toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester (8.6 g, 32 mmol) and K2CO3 (9.5 g, 68.8 mmol) in DMF (50 mL) was heated at 75° C. overnight. After cooled to room temperature, the mixture was poured into water. The aqueous phase was extracted with EtOAc twice. The combined organic phases were washed with water and brine, dried and concentrated. The residue was purified by column chromatography to give the title compound (7.0 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionThe aqueous phase was extracted with EtOAc twice
  3. washThe combined organic phases were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-03039535c79f41ea9209b3568d0e7dd5
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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