Cyclohexanol → 3-Cyclohexyloxy-6,7-dimethoxy-quinoline

HRID 23337

反応式

HRID 23337 の反応式
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2.[CH:16]1(O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:16]1([O:1][C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=3)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

6

反応物 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 100587666,7-Dimethoxyquinolin-3-ol

生成物 1

HCID 99040183-Cyclohexyloxy-6,7-dimethoxy-quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a THF solution (30 mL) at 0° C. is added 3-hydroxy-6,7-dimethoxyquinoline (0.237 g, 1.15 mmol), cyclohexanol (0.347 g, 3.46 mmol), Ph3P (0.908 g, 3.46 mmol). Diethylazodicarboxylate is added portionwise until the solution retained a deep red color (0.663 g, 3.81 mmol). After 4 hours the solution is concentrated and the residue chromatographed (50% EtOAc in hexanes). The product is recrystallized from isopropanol/hexanes as the HCl salt as a white solid (m.p. 229-232° C., dec.).

後処理

  1. concentrationAfter 4 hours the solution is concentrated
  2. customthe residue chromatographed (50% EtOAc in hexanes)
  3. customThe product is recrystallized from isopropanol/hexanes as the HCl salt as a white solid (m.p. 229-232° C., dec.)

出典と根拠

ORDレコード
ord-08e2a2c1bd0947beb25af09a094e127e
出典データセット
uspto-grants-2005_02
特許番号
US06852712B2

関連ノート

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