Tetrahydrofuran → 4-(Methoxymethoxy)-2H-spiro[benzofuran-3,1'-cyclopropane]
Reaction equation
O[CH2:2][C:3]1([C:6]2[C:11]([O:12][CH2:13][O:14][CH3:15])=[CH:10][CH:9]=[CH:8][C:7]=2[OH:16])[CH2:5][CH2:4]1.O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[CH3:15][O:14][CH2:13][O:12][C:11]1[C:6]2[C:3]3([CH2:2][O:16][C:7]=2[CH:8]=[CH:9][CH:10]=1)[CH2:4][CH2:5]3Participants
5
Procedure
To a solution of 2-[1-(hydroxymethyl)cyclopropyl]-3-{[(methyloxy)methyl]oxy}phenol (Reference Intermediate 212, 190 mg) in dry tetrahydrofuran (10 ml) triphenylphosphine (333 mg, 1.271 mmol) was added and the reaction mixture was stirred until complete dissolution of PPh3. DIAD (0.198 ml, 1.017 mmol) was then added dropwise and the reaction mixture was stirred for 30 minutes at room temperature The solvent was removed under reduced pressure. The residue was purified by flash chromatography (Biotage system) on silica gel using a 25 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 9:1 as eluents affording the title compound as a light yellow oil (120 mg).
Workup
- customwas removed under reduced pressure
- customThe residue was purified by flash chromatography (Biotage system) on silica gel using a 25 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 9:1 as eluents
Sources & evidence
- ORD record
- ord-63ac1084b0564c0b93042afe4d2817ef
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216967B2
Reaction notes
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