HCID 54190140, compound → HCID 10690304, compound

HRID 1740271Notes

Reaction equation

HRID 1740271 reaction equation
[Cl:1][C:2]([Cl:22])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([OH:5])=[O:4].[H][H]>C1COCC1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[Cl:1][C:2]([Cl:22])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 54190140HCID 54190140, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10690304HCID 10690304, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.09 g (3.18 mmol) 13 was dissolved in 300 ml THF and hydrogenated for 40 minutes at -40° C. at a hydrogen overpressure of 42 mbar after addition of 200 mg 10% Pd/BaSO4. The catalyst is sucked off and 0.95 g (90%) 14 was obtained as a colourless oil after evaporating the remaining solution. 100 mg (0.29 mmol) 14 was dissolved in 1 ml ethanol, cooled in an ice-bath and admixed with a solution of 12 mg (0.29 mmol) sodium hydroxide in 1 ml ethanol. The sodium salt was precipitated by addition of ether and it was allowed to stand for 12 hours in a refrigerator. The precipitate was suction filtered, washed with cold ether and dried in a vacuum. 100 mg (94%) sodium salt of 14, melting point 157-159° C.

Sources & evidence

ORD record
ord-9ce573b3b3d34635a844158a5e8c1ed7
Source dataset
uspto-grants-1999_10
Patent number
US05968982

Reaction notes

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