HCID 57025558, compound → HCID 15037094, compound

HRID 1109881Notes

Reaction equation

HRID 1109881 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-569e9be1504446a1a887eb9fe1d3a2d6
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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