(1S)-(+)-Camphor-10-sulphonic acid → HCID 58438735, compound

HRID 217457Notes

Reaction equation

HRID 217457 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:17]=[O:18])[C:11]([CH3:16])([CH3:15])[O:12]2)=[CH:7][CH:6]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CCO>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:17]=[O:18])[C:11]([CH3:15])([CH3:16])[O:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 58438670HCID 58438670, compound

Product 1

HCID 58438735HCID 58438735, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

7-(Methoxymethoxy)-2,2-dimethyl-2H-chromene-3-carbaldehyde (300 mg) was dissolved in EtOH (10 mL), and (1S)-(+)-10-camphor sulfonic acid (421 mg) was added thereto, followed by stirring at 80° C. overnight. To the reaction liquid was added silica gel, followed by concentration. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=90:10 to 70:30) to obtain 7-hydroxy-2,2-dimethyl-2H-chromene-3-carbaldehyde (175 mg) as a red powder.

Workup

  1. customTo the reaction liquid
  2. additionwas added silica gel
  3. concentrationfollowed by concentration
  4. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=90:10 to 70:30)

Sources & evidence

ORD record
ord-5da2af6b21a34297b4ee7831ce2ed076
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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