Water → 3,5-Dioxohexanoic acid
Reaction equation
[OH:1][C:2]1[C:3]([C:13]([O:15]CC)=[O:14])=CC2[C:10]([CH:11]=1)=[CH:9]C=C(O)C=2.[I-].C(=O)([O-])[O-:20].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH3:9][C:10]([CH2:11][C:2]([CH2:3][C:13]([OH:15])=[O:14])=[O:1])=[O:20]Participants
7
Conditions
- Temperature
- 55 °C
Procedure
A solution of ethyl 3,7-dihydroxy-2-naphthoate (62 mg, 0.26 mmole) (the acid was obtained from Aldrich and it was converted to the ester using standard techniques) 2 mg, and iodide 2 (242 mg) in dimethylforamide (0.5 ml) was heated at 55° C. with potassium carbonate (175 mg) for 4 hours. An additional amount of the iodide 2 (80 mg) was added to the mixture which was heated at 55° C. overnight. The mixture was worked up with water (50 ml) and ethyl acetate (2×75 ml). The ethyl acetate extracts were washed with brine (30 ml), dried over sodium sulfate, filtered and concentrated. The crude product was purified on a silica gel column (hexane:ethyl acetate, 1.5:1) to provide the triacetate of 17 (130 mg, 65% yield).
Workup
- washThe ethyl acetate extracts were washed with brine (30 ml)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified on a silica gel column (hexane:ethyl acetate, 1.5:1)
Sources & evidence
- ORD record
- ord-80db18392ed54fba8aaff39beb0cf1c8
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05837689
Reaction notes
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