Hepta-1,6-dien-4-ol → HCID 11078067, compound

Reaction equation

[H-].[Na+].[CH2:3]=[CH:4][CH2:5][CH:6]([OH:10])[CH2:7][CH:8]=[CH2:9].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br>C1COCC1>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:10][CH:6]([CH2:7][CH:8]=[CH2:9])[CH2:5][CH:4]=[CH2:3]

Participants

Procedure

8.9 g of 60% sodium hydride was suspended in 100 ml of THF, and 25 g of 1,6-heptadien-4-ol dissolved in 50 ml of THF was dropped therein in an atmosphere of argon. 94 g of 1,10-dibromodecane dissolved in 50 ml of THF was further dropped therein, and reflux was carried out for 13 hours in an atmosphere of argon. After the generated precipitate was filtered off, the solvent was evaporated, and the residue was purified by silica gel column chromatography, to obtain 19 g of the compound (4). (Yield: 26%)