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

HRID 1484632ノート

反応式

HRID 1484632 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cb5f146cfad47a0b27028768bf66ba3
出典データセット
uspto-grants-2016_08
特許番号
US09422272B2

反応ノート

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