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

HRID 2278306ノート

反応式

HRID 2278306 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-93dedab43ce84d76968bcbe0591a6f7f
出典データセット
uspto-grants-2015_09
特許番号
US09133175B2

反応ノート

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