Water → 1-Phenylcyclopentane-1-carbaldehyde

HRID 1427945Notes

Reaction equation

HRID 1427945 reaction equation
[C:1]1([C:7]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)(O)[O-].[Na+].O>C(Cl)Cl>[C:1]1([C:7]2([CH:12]=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 123544(1-Phenylcyclopentyl)methanolHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate

Product 1

HCID 110951241-Phenylcyclopentane-1-carbaldehydeYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-Phenyl-cyclopentyl)-methanol (1.0 g, 5.7 mmol) in DCM (20 mL) was added Dess-Martin Periodine (6.8 mmol, 1.2 eq) and sodium bicarbonate (6.8 mmol, 1.2 eq) at 0° C. The reaction mixture stirred at this temperature for 2 h and allowed to warm up slowly to room temperature. After completion of the reaction, the mixture was poured into water (50 mL) and extracted with DCM (50 mL). The organic mixture was then dried over sodium sulfate and concentrated under reduced pressure to give 1-Phenyl-cyclopentanecarbaldehyde (812 mg) which was immediately used to synthesize title compound (14 mg) from Intermediate B (20 mg, 0.025 mmol) following general procedures D and B. LC-MS (m/z): 923.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with DCM (50 mL)
  3. dry with materialThe organic mixture was then dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6fd1840555894a5f98ff9d4d4230ccae
Source dataset
uspto-grants-2015_01
Patent number
US08933222B2

Reaction notes

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