Tetrahydrofuran → 4-(Methoxymethoxy)-7-methyl-2H-spiro[benzofuran-3,1'-cyclopropane]

HRID 1484632Notes

Reaction equation

HRID 1484632 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]=[C:8]([CH3:16])[C:7]=2[OH:17])[CH2:5][CH2:4]1.O1CCCC1.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:17][C:7]=2[C:8]([CH3:16])=[CH:9][CH:10]=1)[CH2:4][CH2:5]3

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 5363146Diisopropyl azodicarboxylateHCID 866984482-[1-(Hydroxymethyl)cyclopropyl]-3-(methoxymethoxy)-6-methyl-phenol2×

Product 1

HCID 679599444-(Methoxymethoxy)-7-methyl-2H-spiro[benzofuran-3,1'-cyclopropane]Yield 67.3%

Procedure

To a solution of 2-[1-(hydroxymethyl)cyclopropyl]-3-(methoxymethoxy)-6-methyl-phenol (Intermediate 11, 65 mg, 0.27 mmol) in dry tetrahydrofuran (5 ml) triphenylphosphine (84 mg, 0.32 mmol) was added and the reaction mixture was stirred until complete dissolution of it. DIAD (0.056 ml, 0.285 mmol) was then added dropwise and the reaction mixture was stirred for 30 minutes at room temperature. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 8:2 as eluents affording the title compound (40 mg) as a light yellow oil.

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes at room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 8:2 as eluents

Sources & evidence

ORD record
ord-3cb5f146cfad47a0b27028768bf66ba3
Source dataset
uspto-grants-2016_08
Patent number
US09422272B2

Reaction notes

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