4(2H)-Benzofuranone, 2-ethoxy-3,5,6,7-tetrahydro- → HCID 68282353, compound

HRID 571139Notes

Reaction equation

HRID 571139 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:8][C:7]2[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]=2[O:5]1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][CH:4]1[CH2:8][CH:7]2[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][CH:6]2[O:5]1)[CH3:2]

Participants

4

Reactant 1

HCID 110630394(2H)-Benzofuranone, 2-ethoxy-3,5,6,7-tetrahydro-

Product 1

HCID 68282353HCID 68282353, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the ketone 10 (140 mg, 0.77 mmol) in EtOAc (9 mL) was added 5% Pd/C (128 mg, 60 μmol) and the mixture was stirred under H2 (1 atm) for 1.5 h at room temperature. The mixture was then filtered on Celite and the pad washed with EtOAc. Evaporation of the solvent furnished the corresponding crude ketone 11 as an essentially pure mixture of diastereoisomers (130 mg, dr=9:1). The ketone was directly submitted to the next step without purification. TLC Major isomer: Rf=0.35 (hexanes:EtOAc=2:1).

Workup

  1. filtrationThe mixture was then filtered on Celite
  2. washthe pad washed with EtOAc
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-05d8086049b249f9a5fee86916f433c0
Source dataset
uspto-grants-2015_05
Patent number
US09024038B2

Reaction notes

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