Methanol → 7-Hydroxy-3-methoxybicyclo[4,3,0]non-3-ene

HRID 462780Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH2:14][CH:15]2[CH:19]([CH2:20][CH:21]=1)[C:18](=[O:22])[CH2:17][CH2:16]2.CO.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[OH:22][CH:18]1[CH2:17][CH2:16][CH:15]2[CH:19]1[CH2:20][CH:21]=[C:13]([O:12][CH3:11])[CH2:14]2

Participants

Conditions

Temperature: -10 °C

Procedure

Diisobutylaluminium hydride (28.5 ml) was added dropwise to a stirred solution of 3-methoxybicyclo[4,3,0]non-3-en-7-one (20 g; prepared as described in Reference Example 1) in diethyl ether (600 ml), with cooling to -10° C. The resulting solution was stirred at 0° C. for 3 hours and then it was treated with methanol (20 ml). A gelatinous precipitate was formed, and the mixture was then treated with anhydrous sodium sulphate (200 g) and filtered with the aid of diatomaceous earth. The filtrate was concentrated at reduced pressure, to give 7-hydroxy-3-methoxybicyclo[4,3,0]non-3-ene (16 g).

Workup

customA gelatinous precipitate was formed
filtrationfiltered with the aid of diatomaceous earth
concentrationThe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record: ord-8aa9fcbff6394c6687bf469fa036fba3
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04517202

Reaction notes

Loading…