HCID 86758362, compound → HCID 18467805, compound

HRID 2229489Notes

Reaction equation

HRID 2229489 reaction equation
[CH3:1][C:2]1([C:13]([O:15]C(C)(C)C)=[O:14])[C:6](=[CH:7][C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH:4]([CH3:12])[O:3]1.[H][H]>C(OCC)(=O)C.CO>[CH3:1][C:2]1([C:13]([OH:15])=[O:14])[CH:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH:4]([CH3:12])[O:3]1

Participants

5

Reactant 2

HCID 86758362HCID 86758362, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18467805HCID 18467805, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,5-Dimethyl-3-methoxycarbonylmethylene-2-tetrahydrofuroic acid, t-butyl ester (28 mg, obtained from Step A) was dissolved in 0.25 mL of ethyl acetate and 0.25 mL of methanol. This mixture was hydrogenated under a balloon of hydrogen at room temperature for 1.25 h. The reaction mixture was filtered over a pad of celite, and the crude product obtained after removal of volatiles was purified via a silica gel SepPak, providing 21 mg of the desired compound cleanly (75% yield), homogeneous by TLC (Rf=0.2 in 10/1 hexane/ethyl acetate)

Workup

  1. filtrationThe reaction mixture was filtered over a pad of celite
  2. customthe crude product obtained
  3. customafter removal of volatiles
  4. customwas purified via a silica gel SepPak

Sources & evidence

ORD record
ord-1e5a2b6a049b4681b663d852fd9fdc6b
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

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