Benzyl Alcohol → HCID 86590900, compound

HRID 1793318Notes

Reaction equation

HRID 1793318 reaction equation
C1COCC1.[C:6]1([CH2:12][OH:13])[CH:11]=[CH:10][CH:9]=[CH:8]C=1.[OH-].[Na+].[Cl:16][C:17]1[C:22]([O:23][CH2:24][CH:25]2[CH2:27][O:26]2)=[CH:21][CH:20]=[CH:19][N:18]=1>O>[Cl:16][C:17]1[C:22]([O:23][CH2:24][CH:25]([OH:26])[CH2:27][O:13][CH2:12][CH2:6]/[CH:11]=[CH:10]\[CH:9]=[CH2:8])=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11789921HCID 11789921, compound

Product 1

HCID 86590900HCID 86590900, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of THF (915 ml), benzenemethanol (2.96 mol) and NaOH (2.36 mol) was stirred at room temperature for 30 minutes (cooling was required to keep the temperature below 25° C.). Intermediate (19) (1.97 mol) was added. The reaction mixture was stirred at room temperature for 4 days. Water was added dropwise (cooling required) and the mixture was extracted with ethyl acetate. The organic layer was dried, filtered and the solvent was evaporated. The residue was combined with analogously obtained fraction, then purified by HPLC over silica gel (eluent: hexane/ethyl acetate (60/40)). The desired fractions were collected and the solvent was evaporated, yielding 38% of 1-[(2-chloro-3-pyridinyl)oxy]-3-[(3Z)-3,5-hexadienyloxy]-2-propanol (intermediate 20).

Workup

  1. temperaturecooling
  2. customthe temperature below 25° C.
  3. stirringThe reaction mixture was stirred at room temperature for 4 days
  4. temperature(cooling required)
  5. extractionthe mixture was extracted with ethyl acetate
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. custompurified by HPLC over silica gel (eluent: hexane/ethyl acetate (60/40))
  10. customThe desired fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f0951644cba643059e43008a1e0b23cf
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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