Cornforth reagent → Spiro(2.5)octane-6-carbaldehyde

HRID 15289

Reaction equation

HRID 15289 reaction equation
[CH2:1]1[C:3]2([CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]2)[CH2:2]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:2]1[C:3]2([CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]2)[CH2:1]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 53487089(Spiro(2.5)octan-6-yl)methanol

Product 1

HCID 86598198Spiro(2.5)octane-6-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Spiro[2.5]oct-6-yl-methanol (2.57 g, 18.3 mmol, 1.0 eq.) was dissolved in CH2Cl2 (30 mL) and placed in a ice-water bath at 0° C. Pyridinium dichromate (PCC) (7.9 g, 36.6 mmol, 2.0 eq.) was added and the reaction warmed to room temperature for 4 hours with stirring. The crude reaction was filtered through a Celite pad and washed with CH2Cl2 and evaporated. The crude material was dissolved in diethyl ether and filtered through Celite, washing with diethyl ether several times. Evaporated solvent to provide Spiro[2.5]octane-6-carbaldehyde as a brown oil (2.98 g, quantitative) that was used directly. 1H NMR (CHCl3, 400 MHz) δ 0.17-0.27 (m, 4H), 0.88-0.91 (m, 2H), 1.09-1.25 (m, 2H), 1.52-1.54 (m, 2H), 1.69-1.75 (m, 3H), 9.44 (d, 1H, J=1.2 Hz).

Workup

  1. customplaced in a ice-water bath at 0° C
  2. customThe crude reaction
  3. filtrationwas filtered through a Celite pad
  4. washwashed with CH2Cl2
  5. customevaporated
  6. dissolutionThe crude material was dissolved in diethyl ether
  7. filtrationfiltered through Celite
  8. washwashing with diethyl ether several times

Sources & evidence

ORD record
ord-c30f4ecb7f5a47108df6f7c307355618
Source dataset
uspto-grants-2010_06
Patent number
US07732449B2

Linked notes

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