Triphenylphosphine → 5,6-Dihydroimidazo[1,5-d][1,4]benzoxazepine

HRID 404255ノート

反応式

HRID 404255 の反応式
O[CH2:2][CH2:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:7][N:6]=[CH:5]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:7]1[N:6]=[CH:5][N:4]2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:2][CH2:3]2

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 582941362-(1-(2-hydroxyethyl)-1H-imidazol-5-yl)phenol

生成物 1

HCID 582941105,6-Dihydroimidazo[1,5-d][1,4]benzoxazepine収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 2-(1-(2-hydroxyethyl)-1H-imidazol-5-yl)phenol (103.0 mg, 0.5 mmol) and PPh3 (157.0 mg, 0.6 mmol) in THF (4 mL) at 0° C., was added DEAD (0.22 mL, 40% solution in toluene, 0.75 mmol). The resulting yellow solution was allowed to warm to rt and stirred overnight. The solvent was removed under reduced pressure and the crude residue was purified by flash column chromatography on silica gel to afford the desired product in 84% yield. 1H NMR: 4.35-4.45 (m, 4H), 6.94-7.05 (m, 2H), 7.11-7.19 (m, 1H), 7.43 (d, 1H, J=0.8 Hz), 7.49 (s, 1H), 7.67 (dd, 1H, J=1.6, 8.0 Hz).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe crude residue was purified by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-b5afb2c1b9e847f791564d107c9f3382
出典データセット
uspto-grants-2014_06
特許番号
US08748469B2

反応ノート

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