2,6-Lutidine → 3-(Tetrahydro-2-furanyl)phenylmethanol
Reaction equation
[O:1]1[CH:5]=[CH:4][CH2:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].N1C(C)=CC=CC=1C.[H][H]>C1COCC1>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:11]=[CH:12][CH:13]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
EX-608C) A THF (15 mL) solution of the aldehyde from EX-608B (0.70 g, 4.0 mmol) and 2,6-lutidine (0.46 mL, 4.0 mmol) was stirred in a hydrogen 4.0 mmol) and 2,6-lutidine (0.46 mL, 4.0 mmol) was stirred in a hydrogen temperature. The slurry was filtered through celite, and the solvent was removed. The residue was taken up in ethyl acetate and washed with 1 N HCl and brine. The organic layer was dried (MgSO4) and evaporated to give 0.50 g (70%) of the desired 3-(tetrahydro-2-furanyl)phenylmethanol product as a yellow oil. The formation of the desired product was monitored by the disappearance of the aldehyde (δ˜10) and olefin peaks in the 1H NMR disappearance of the aldehyde (δ˜10) and olefin peaks in the 1H NMR spectrum. 2.8 mmol) and MnO2 (2.10 g, 24.3 mmol) in dichloromethane (15 mL) was refluxed for 3 h. The slurry was filtered through celite, and the filtrate was evaporated to a yellow oil. Purification by flash chromatography on silica gel eluting with 10% ethyl acetate in hexane gave 0.19 g (45%) of the desired aldehyde product as a pale yellow oil. GCMS: m/z=177 [M+H]+.
Workup
- filtrationThe slurry was filtered through celite
- customthe solvent was removed
- washwashed with 1 N HCl and brine
- dry with materialThe organic layer was dried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-3dee1f0e56624a0aadeef21c471b62d3
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06458803B1
Reaction notes
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