6,6-Diethoxy-4-hexyn-3-ol → 6,6-Diethoxy-hex-4-yn-3-one

HRID 1952624Notes

Reaction equation

HRID 1952624 reaction equation
[CH2:1]([O:3][CH:4]([O:11][CH2:12][CH3:13])[C:5]#[C:6][CH:7]([OH:10])[CH2:8][CH3:9])[CH3:2]>ClCCl.O=[Mn]=O>[CH2:12]([O:11][CH:4]([O:3][CH2:1][CH3:2])[C:5]#[C:6][C:7](=[O:10])[CH2:8][CH3:9])[CH3:13]

Participants

4

Reactant 1

HCID 664867606,6-Diethoxy-4-hexyn-3-ol

Product 1

HCID 866712646,6-Diethoxy-hex-4-yn-3-oneYield 34.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

6,6-Diethoxy-hex-4-yn-3-ol (4.30 g, 23.1 mmol) was dissolved in dichloromethane (200 ml) and treated with activated MnO2 (50 g) at rt for 15 h. The reaction mixture was filtered through a plug of celite and Na2SO4. The filtrated was concentrated under reduced pressure and purified by flash chromatography with 0-20% EtOAc in hexane to afford the desired product (1.46 g, 34% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite and Na2SO4
  2. concentrationThe filtrated was concentrated under reduced pressure
  3. custompurified by flash chromatography with 0-20% EtOAc in hexane

Sources & evidence

ORD record
ord-cad4f8c0140e4a53a9f1d98f961fb41d
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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