HCID 15341785, compound → HCID 15341786, compound

HRID 1756183Notes

Reaction equation

HRID 1756183 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:22]=[CH:21][C:9]2[C:10](=O)[CH:11]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[O:13][C:8]=2[C:7]=1[CH2:23][CH2:24][CH3:25]>C(OCC)(=O)C.P(=O)(O)(O)O.[Pd]>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:22]=[CH:21][C:9]2[CH2:10][CH2:11][CH:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[O:13][C:8]=2[C:7]=1[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 1

HCID 15341785HCID 15341785, compound

Product 1

HCID 15341786HCID 15341786, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1004Phosphoric AcidSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Methyl 7-(3-chloropropoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-propanoate (2.0 g, 5.35 mmol) was dissolved in a mixture of 25 ml ethyl acetate and 0.32 ml phosphoric acid and hydrogenated at 5 psi and 25° C. using 2 g of 5% Pd/C as catalyst. The product was dissolved in ethyl acetate, washed with 10% sodium carbonate solution, then washed once with water, dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give the product as a colorless oil (1.5 gm, 90% yield).

Workup

  1. washwashed with 10% sodium carbonate solution
  2. washwashed once with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-55d98ea13c644f2db806c3c4d32681a0
Source dataset
uspto-grants-1995_08
Patent number
US05439937

Reaction notes

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