6,6-Diethoxy-2-methyl-hex-4-yn-3-ol → 6,6-Diethoxy-2-methylhex-4-yn-3-one

HRID 1952612Notes

Reaction equation

HRID 1952612 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]#[C:6][CH:7]([OH:11])[CH:8]([CH3:10])[CH3:9])[CH3:2]>ClCCl.O=[Mn]=O>[CH2:13]([O:12][CH:4]([O:3][CH2:1][CH3:2])[C:5]#[C:6][C:7](=[O:11])[CH:8]([CH3:9])[CH3:10])[CH3:14]

Participants

4

Reactant 1

HCID 130660616,6-Diethoxy-2-methyl-hex-4-yn-3-ol

Product 1

HCID 3414396,6-Diethoxy-2-methylhex-4-yn-3-oneYield 36.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

6,6-Diethoxy-2-methyl-hex-4-yn-3-ol (3.18 g, 18.46 mmol) was dissolved in dichloromethane (100 ml) and treated with activated MnO2 (30 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 0-15% EtOAc in hexane to afford the desired product (1.32 g, 36% 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 0-15% EtOAc in hexane

Sources & evidence

ORD record
ord-6917c6e2db0f43979b00945d5bb17cb2
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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