2-(But-3-en-1-yloxy)cyclohexanol → 2-(But-3-en-1-yloxy)cyclohexanone

HRID 73617Notes

Reaction equation

HRID 73617 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH2:12]([O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[OH:23])[CH2:13][CH:14]=[CH2:15]>C(Cl)Cl>[CH2:12]([O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:23])[CH2:13][CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 665775152-(But-3-en-1-yloxy)cyclohexanolHCID 178418287HCID 178418287, compound

Product 1

HCID 665774622-(But-3-en-1-yloxy)cyclohexanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of PCC (26.6 g, 123 mmol) in CH2Cl2 (160 mL) was added 2-(but-3-en-1-yloxy)cyclohexanol (7 g, 41 mmol) in CH2Cl2 (10 mL). The reaction was stirred at rt overnight. The mixture was filtered through a pad of celite and washed with CH2Cl2. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.75-5.90 (m, 1H), 4.95-5.15 (m, 2H), 3.78 (dd, 1H, J=5.37 Hz, 9.76 Hz), 3.65-3.70 (m, 1H), 3.39-3.45 (m, 1H), 1.05-2.58 (m, 10H).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashed with CH2Cl2
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0c19087223614f2094bc3923bd526f79
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

Loading…