Water → HCID 23459796, compound

HRID 2287201Notes

Reaction equation

HRID 2287201 reaction equation
C[O:2][C:3]1[C:16]2[C:15](=[O:17])[CH:14]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[O:12][C:11]=2[C:10]([CH2:22][CH2:23][CH3:24])=[C:9]2[C:4]=1[C:5](=[O:25])[CH2:6][CH2:7][CH2:8]2.[I-].[K+].O>C(O)=O>[OH:2][C:3]1[C:16]2[C:15](=[O:17])[CH:14]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[O:12][C:11]=2[C:10]([CH2:22][CH2:23][CH3:24])=[C:9]2[C:4]=1[C:5](=[O:25])[CH2:6][CH2:7][CH2:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 4875Potassium IodideHCID 23459803Methyl 6,7,8,9-tetrahydro-5-methoxy-4,6-dioxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylate

Product 1

HCID 23459796HCID 23459796, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Methyl 6,7,8,9-tetrahydro-5-methoxy-4,6-dioxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylate (172 mg; 0.5 mmole) in formic acid (5 ml) was heated on a steam bath with ground potassium iodide (800 mg; 4.8 mmole) for 1 hour. The mixture was poured into water and extracted with ethylacetate (3×). The organic fractions were washed with water and dried (sodium sulphate) to yield a brown oil (180 mg) which crystallised on trituration with ethanol. The solid was filtered off and washed with a little ether to give the title compound as a yellow powder (110 mg; 67%) mp 200° (decomposition).

Workup

  1. extractionextracted with ethylacetate (3×)
  2. washThe organic fractions were washed with water
  3. dry with materialdried (sodium sulphate)

Sources & evidence

ORD record
ord-cccd5b8d9eed4b26b81527f5a77b4f57
Source dataset
uspto-grants-1981_05
Patent number
US04269854

Reaction notes

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