HCID 57025558, compound → HCID 15037094, compound

HRID 1090901Notes

Reaction equation

HRID 1090901 reaction equation
[O:1]=[C:2]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:3]=[CH:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([Si:12]([CH3:15])([CH3:14])[CH3:13])[O:10][CH:11]=1.[H][H]>C(OCC)(=O)C.[Pt]=O>[O:1]=[C:2]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([Si:12]([CH3:13])([CH3:15])[CH3:14])[O:10][CH:11]=1

Participants

5

Reactant 2

HCID 57025558HCID 57025558, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15037094HCID 15037094, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 4-(5-oxo-3-hexadecenyl)-2-trimethylsilylfuran (98 mg, 0.261 mmol), prepared as in Example 3, in ethyl acetate (2 ml) was added platinum oxide (10 mg, 0.044 mmol). This mixture was subjected to one atmosphere of hydrogen at room temperature with stirring for 21/2 hours. The reaction mixture was filtered and concentrated to give a yellow oil. Purification by flash chromatography (silica, 3% ethyl ether/hexane) gave the desired ketone.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto give a yellow oil
  4. customPurification by flash chromatography (silica, 3% ethyl ether/hexane)

Sources & evidence

ORD record
ord-fbf9e3691acd4472ab1fd2ec43463f68
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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