Pyridine → (4aR,8aS)-2,6-Bis(hydroxymethylidene)octahydronaphthalene-1,5-dione

Participants

Reaction Steps

A mixture of 1.66 g (10 mmole) of trans-decalin-1,5-dione, 2.16 g (40 mmole) of NaOCH3, 9.2 ml (130 mmole) of ethyl formate, and 70 ml of dry pyridine was stirred under nitrogen at room temperature for 21 hr. After the mixture was adjusted to a pH between 5 and 6 with the aid of 51 ml of AcOH and 471 ml of water, it was extracted with benzene several times. The benzene layers were thoroughly washed with water and then were extracted with 2% KOH solution. The basic extracts were washed with ether and then after reacidification with AcOH they were thoroughly extracted again with benzene. The benzene extracts were dried (Na2SO4) and then were reduced to dryness to give 2 g (90%) of crude product. Recrystallization from ethanol afforded trans-2,6-Bis(hydroxymethylene)decalin-1,5-dione as a fine yellow powder, mp 155°-157°; ir (nujol) 1640 and 1570 cm-1 ; nmr (CDCl3)δ2.3 (broad multiplet, 10), 9.00 (s,2), and 14.50 (s,2); mass spectrum m/e 222(M+.).

Provenance & Evidence