Diethyl Ether → HCID 11564564, compound

HRID 78956Notes

Reaction equation

HRID 78956 reaction equation
[CH:1]1([CH2:7][CH:8]([OH:13])[CH2:9][CH2:10][CH:11]=[CH2:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.CCOCC>C(Cl)Cl>[CH:1]1([CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH:11]=[CH2:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 66839522HCID 66839522, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 11564564HCID 11564564, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-cyclohexyl-5-hexen-2-ol (2.75 g, 15 mmol; prepared according to X. Wang et al, in Org. Lett., 2003, 5, 2699, supplementary materials) in CH2Cl2 (5 ml) was added to a suspension of PCC (4.9 g, 22 mmol) and Celite® (7.35 g) in CH2Cl2 (70 ml) at 20°. After 4 hours at that temperature, 10 mol % of PCC was added and after a supplementary hour Et2O was added and the reaction filtrated over SiO2 before to be concentrated. Purification by chromatography on silica with cyclohexane/AcOEt 95:5 afforded the desired ketone in 73% yield.

Workup

  1. additionwas added
  2. filtrationthe reaction filtrated over SiO2 before
  3. concentrationto be concentrated
  4. customPurification by chromatography on silica with cyclohexane/AcOEt 95:5

Sources & evidence

ORD record
ord-19acda7b77694a4489c8c4c16726b32b
Source dataset
uspto-grants-2014_09
Patent number
US08841488B2

Reaction notes

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