Tetrapropylammonium → (S)-9-hydroxy-5,9-dimethyl-decanal

HRID 1740545Notes

Reaction equation

HRID 1740545 reaction equation
C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC.[CH3:22][C@@H:23]([CH2:29][CH2:30][CH2:31][C:32]([CH3:35])([OH:34])[CH3:33])[CH2:24][CH2:25][CH2:26][CH2:27][OH:28]>C(Cl)Cl>[OH:34][C:32]([CH3:33])([CH3:35])[CH2:31][CH2:30][CH2:29][C@H:23]([CH3:22])[CH2:24][CH2:25][CH2:26][CH:27]=[O:28]

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 15859989(R)-5,9-dimethyl-decane-1,9-diol

Product 1

HCID 54287074(S)-9-hydroxy-5,9-dimethyl-decanalYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.68 g of 4-methylmorpholine N-oxide (monohydrate) (NMO) and 31.5 g of molecular sieves (powder, 4A) in 200 ml of abs. CH2Cl2 were stirred for 0.25 h at ambient temperature. 500 mg of tetrapropylammonium perrhutenate (TPAP) was added, before a solution of 4.59 g of (R)-5,9-dimethyl-decane-1,9-diol in 20 ml of abs. CH2Cl2 was added within 1 h. 15 minutes later, the reaction mixture was filtered and the solvents removed i.V. Flash chromatography (SiO2, hexane/AcOEt=7/3) afforded 3.103 g of (S)-9-hydroxy-5,9-dimethyl-decanal as colorless oil, 98.7% pure according to GC.

Workup

  1. filtration15 minutes later, the reaction mixture was filtered
  2. customthe solvents removed i.V

Sources & evidence

ORD record
ord-28dc91950efb478e96130cd473239899
Source dataset
uspto-grants-1999_10
Patent number
US05969190

Reaction notes

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