HCID 13911126, compound → 3,5-Dioxohexanoic acid

HRID 651950Notes

Reaction equation

HRID 651950 reaction equation
[O:1]1[C@H:3]2[C:4](=[O:30])C=C3[C@:27](C)([C@@H:2]12)[C@@H]1[C@H]([C@H]2[C@](C)(CC1)[C@@H]([C@H](C)CCCC(O)(C)C)CC2)C=C3.C([O:34][C:35](=[O:37])[CH3:36])(=O)C.N1C=CC=CC=1>>[CH3:27][C:2]([CH2:3][C:4]([CH2:36][C:35]([OH:34])=[O:37])=[O:30])=[O:1]

Participants

3

Reactant 2

HCID 13911126HCID 13911126, compoundHCID 22348678Acetic anhydride pyridine

Product 1

HCID 54598443,5-Dioxohexanoic acid

Procedure

The cholest-5-ene from Example 4 (c) was acetylated with acetic anhydride/pyridine to yield the triacetate which was subjected to bromination with dibromodimethylhydantoin followed by dehydrobromination with trimethylphosphite according to the procedure of Example 3 (b) to yield, after chromatography on silver nitrate impregnated silica gel, 1α,3β,25-triacetoxycholesta-5,7-diene (m.p. 96°-101°; αD -24° in CHCl3 ; λmaxEt2O 262 (7,900), 271 (11,500), 282 (12,400), 294 (7,300) nm.

Sources & evidence

ORD record
ord-1246c53baa3146d3af64381e908e31ec
Source dataset
uspto-grants-1987_06
Patent number
US04670190

Reaction notes

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