Triphenylphosphine → 2-[9-(1H-pyrazol-1-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde

HRID 2167037Notes

Reaction equation

HRID 2167037 reaction equation
[CH2:1]([C:4]1([N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)[CH2:13][C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[O:7][CH2:6][CH2:5]1)[CH:2]=C.[O:19]=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[N:14]1([C:4]2([CH2:1][CH:2]=[O:19])[CH2:13][C:8]3([CH2:12][CH2:11][CH2:10][CH2:9]3)[O:7][CH2:6][CH2:5]2)[CH:18]=[CH:17][CH:16]=[N:15]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 683141651-[9-(prop-2-en-1-yl)-6-oxaspiro[4.5]decan-9-yl]-1H-pyrazole

Product 1

HCID 866714282-[9-(1H-pyrazol-1-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehydeYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[9-(prop-2-en-1-yl)-6-oxaspiro[4.5]decan-9-yl]-1H-pyrazole (80 mg, 0.32 mmol) in DCM (5 mL) at −78° C. was bubbled with O3 until the solution turned blue. The resulting solution was bubbled with N2 for 5 min. To it was added PPh3 (168 mg, 0.64 mmol). And the solution was stirred for 4 h at rt. After removal of the solvent, the residue was purified by flash column chromatography to give 2-[9-(1H-pyrazol-1-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde (15 mg, 23% yield). LCMS m/z 249 (M+1) observed.

Workup

  1. customThe resulting solution was bubbled with N2 for 5 min
  2. customAfter removal of the solvent
  3. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-0797b986dc4c418fba2315a98c4400b5
Source dataset
uspto-grants-2015_06
Patent number
US09044469B2

Reaction notes

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