Hydrochloric Acid → HCID 68514299, compound

HRID 1877036Notes

Reaction equation

HRID 1877036 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:5][C:6]=1[CH:7]([CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1.[OH-].[Li+].O.Cl>CO.O1CCCC1>[CH3:1][C:2]1[O:3][C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:5][C:6]=1[CH:7]([CH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1)[O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 68514226HCID 68514226, compound

Product 1

HCID 68514299HCID 68514299, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methanol (545 mg) obtained by the above-mentioned reaction and methyl 4-hydroxybenzoate (365 mg) in tetrahydrofuran (20 mL) were added tributylphosphine (1.0 mL) and 1,1′-(azodicarbonyl)dipiperidine (1.0 g), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (0% ethyl acetate/hexane to 30% ethyl acetate/hexane) to give methyl 4-[(2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methoxy]benzoate as an oil. The obtained methyl 4-[(2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methoxy]benzoate was dissolved in methanol (4 mL) and tetrahydrofuran (4 mL). 2N Lithium hydroxide (2.0 mL) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (361 mg, 47%) as an amorphous compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d3c15efb322644f0b538fbc4726c1042
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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