HCID 54161724, compound → HCID 53722996, compound

HRID 520434Notes

Reaction equation

HRID 520434 reaction equation
[CH:1]([C:3]1([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:5][CH2:4]1)=[CH2:2]>C(OCC)(=O)C.[Pt](=O)=O>[CH2:1]([C:3]1([C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 54161724HCID 54161724, compound

Product 1

HCID 53722996HCID 53722996, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of benzyl 1-vinylcyclopropanecarboxylate B-40a (100 mg, 0.494 mmol) in ethyl acetate (10 mL) was added platinum (IV) oxide (28.1 mg, 0.124 mmol). The reaction mixture was stirred for 1 h at 25° C. under hydrogen atmosphere (bladder pressure). After completion of reaction, it was filtered through the celite bed and washed the bed with EtOAc (2×20 mL). The solvent was removed under reduced pressure to obtain benzyl 1-ethyl-cyclopropanecarboxylate B-42a (70 mg, 0.343 mmol, 69.3% yield) as a colorless liquid. 1H NMR (CDCl3, δ=7.26 ppm, 400 MHz): δ 7.36-7.30 (m, 5H), 5.10 (s, 2H), 1.59 (q, J=7.2 Hz, 2H), 1.21 (app. q, J≈3.6 Hz, 2H), 0.99 (t, J=7.2 Hz, 3H), 0.69 (app. q, J≈3.6 Hz, 2H).

Workup

  1. customAfter completion of reaction, it
  2. filtrationwas filtered through the celite bed
  3. washwashed the bed with EtOAc (2×20 mL)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5ea0c8557bac4fbcb594ea0b80831309
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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