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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (S)-6-Hydroxy-2,6-dimethyl-heptanal

HRID 493065
Notes
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Reaction equation

HRID 493065 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][CH:23]([CH2:26][CH2:27][CH2:28][C:29]([CH3:32])([OH:31])[CH3:30])[CH2:24][OH:25].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[OH:31][C:29]([CH3:30])([CH3:32])[CH2:28][CH2:27][CH2:26][C@H:23]([CH3:22])[CH:24]=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 2724130Cornforth reagentHCID 20554058HCID 20554058, compound

Product 1

HCID 57680495(S)-6-Hydroxy-2,6-dimethyl-heptanalYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium dichromate (1.5 g, 3.75 mmol) was added to a stirred solution of diol 8 (110 mg, 0.69 mmol) and pyridinium p-toluenesulfonate (33 mg, 0.11 mmol) in CH2Cl2 (5 mL). The resulting suspension was stirred for 4 hours at room temperature under argon. The reaction was then filtered through Celite and solvent was evaporated under reduced pressure. The residue was chromatographed on silica gel using hexane/EtOAc (9:1) as an eluent to give an oily aldehyde 9 (65 mg, 60%).

Workup

  1. filtrationThe reaction was then filtered through Celite and solvent
  2. customwas evaporated under reduced pressure
  3. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-631fb9d9bb224b79b8cda3ab7336246a
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07534777B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes