6-Hydroxyquinoline → HCID 13663813, compound
Reaction equation
[C:1]12([CH2:11]O)C[CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)C1)[CH2:8]2.[OH:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[CH:17]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:43](C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:20]1[C:21]2[C:16](=[CH:15][C:14]([O:13][C:5]3[CH:6]=[C:7]4[C:9](=[CH:3][CH:4]=3)[N:43]=[CH:11][CH:1]=[CH:8]4)=[CH:23][CH:22]=2)[CH:17]=[CH:18][CH:19]=1Participants
Procedure
A mixture of 1-adamantanemethanol (5.00 g, 30.0 mmol) and 6-hydroxyquinoline (13.1 g, 90.2 mmol) in tetrahydrofuran (75 mL) was stirred for 15 min. Then, triphenylphosphine (10.2 g, 39.0 mmol) was added, followed by diethyl azodicarboxylate (6.14 mL, 39.0 mmol). The reaction mixture was refluxed for 18 h. The solvent was then removed by rotary evaporation. The resulting gel was filtered through paper with diethyl ether (3×25 mL). The filtrate was rotary evaporated, and the resulting gel was filtered through paper with hexanes (3×25 mL). Again the filtrate was rotary evaporated, the resulting gel was filtered through paper with hexanes (3×25 mL), and the filtrate was rotary evaporated. This provided 3.8 g (43%) of crude product as a red oil. This oil was chromatographed (2:1 hexanes/ethyl acetate) to provide 1.6 g (18%) of (94):
Workup
- temperatureThe reaction mixture was refluxed for 18 h
- customThe solvent was then removed by rotary evaporation
- filtrationThe resulting gel was filtered through paper with diethyl ether (3×25 mL)
- filtrationthe resulting gel was filtered through paper with hexanes (3×25 mL)
- filtrationthe resulting gel was filtered through paper with hexanes (3×25 mL)
- customThis oil was chromatographed (2:1 hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-bd2a009fabfa4c7c96222518a365b5fd
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07053104B2
Reaction notes
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