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

HRID 1484632노트

반응식

HRID 1484632 반응식
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

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 5363146Diisopropyl azodicarboxylateHCID 866984482-[1-(Hydroxymethyl)cyclopropyl]-3-(methoxymethoxy)-6-methyl-phenol2회

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3cb5f146cfad47a0b27028768bf66ba3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422272B2

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