Tetrahydrofuran → HCID 20231641, compound
Reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[OH2:7].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.[O:19]1[CH2:23]CCC1>>[O:19]1[CH:23]=[CH:9][CH:10]=[C:11]1[CH:12]([O:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[CH2:13][C:8]#[CH:18]Participants
Procedure
To a solution of 10 g (0.073 mole) of the title compound of Example 1 in 40 ml of tetrahydrofuran is added 10 g (0.12 mole) of dihydropyran and 100 mg of p-toluenesulfonic acid monohydrate. The reaction mixture is stirred at room temperature for 4 hours, then diluted with water and 5 ml of 5% aqueous sodium hydroxide. After removal of the solvent, the residue is extracted three times with diethyl ether. The organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The residue is chromatographed on silica gel (using ethyl acetate/hexane as eluent) to give the title compound NMR: 2.78 (d of d, J=6, 2.5 Hz, --CH2 --C≡), 1.92 (t, J=2 Hz, ≡CH), 3.18-4.08 (mult, --CH2 --O), 7.49 and 6.33 ppm (furan). ##STR18##
Sources & evidence
- ORD record
- ord-28fada0547094f099fdeeab9d6c36d06
- Source dataset
- uspto-grants-1986_10
- Patent number
- US04617411
Reaction notes
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