20039-37-6 → HCID 57097671, compound

HRID 2211329Notes

Reaction equation

HRID 2211329 reaction equation
[CH3:1][C@@:2]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]2[OH:9].[Cr](O[Cr](O)(=O)=O)(O)(=O)=O.N1C=CC=CC=1>C(Cl)Cl.C(OCC)C>[CH3:1][C@@:2]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][C:3]2=[O:9]

Participants

5

Reactant 2

HCID 1875720820039-37-6HCID 57313420HCID 57313420, compound

Product 1

HCID 57097671HCID 57097671, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

79.6 g (0.63M) of the optically active alcohol (V) obtained in 1-4) above was dissolved in 300 ml of methylene chloride and the resulting solution was added dropwise to a suspension of 304 g (0.81M) of pyridine dichromate in 700 ml of methylene chloride at room temperature. Then the resulting mixture was stirred for three days. The obtained reaction mixture was diluted with 1 l of diethyl ether and filtered through celite. The filtrate was dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was distilled under reduced pressure to give 50.4 g (theoretical yield: 64.5%) of the aimed compound (VI) as a colorless oily material. b.p.: 70° C./20 mmHg.

Workup

  1. customThe obtained reaction mixture
  2. filtrationfiltered through celite
  3. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-08c384a4b6ec466aa3f88e5e2a55a50b
Source dataset
uspto-grants-1995_10
Patent number
US05463118

Reaction notes

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