Methylenechloride Hexane → HCID 21459577, compound

HRID 1941019Notes

Reaction equation

HRID 1941019 reaction equation
[CH3:1][C:2]12[CH2:27][CH:5]([C:6]3([CH3:26])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([CH:16]([OH:25])[C:17]4[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=4)[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCCCCC.C(Cl)Cl>C(Cl)Cl>[CH3:1][C:2]12[CH2:27][CH:5]([C:6]3([CH3:26])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([C:16]([C:17]4[CH:18]=[CH:19][C:20]([CH:23]=[O:24])=[CH:21][CH:22]=4)=[O:25])[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 21226440Methylenechloride HexaneHCID 21459583HCID 21459583, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 21459577HCID 21459577, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.1 g (8.5 mmol) of the diol obtained in Example 10, in solution in 60 ml of CH2Cl2, were treated with 5.5 g of pyridinium chlorochromate. The reaction mixture was maintained under stirring at room temperature for 3 hours. The reaction mixture was then filtered through Celite. The organic phase was washed with a saturated ammonium chloride solution, rinsed with water, dried and evaporated to yield, after chromatography on silica in a CH2Cl2 /hexane (9/1) eluent mixture, 2 g (66%) of the expected compound, melting at 138°-142° C.

Workup

  1. temperatureThe reaction mixture was maintained
  2. filtrationThe reaction mixture was then filtered through Celite
  3. washThe organic phase was washed with a saturated ammonium chloride solution
  4. washrinsed with water
  5. customdried
  6. customevaporated
  7. customto yield

Sources & evidence

ORD record
ord-08af8c04a70842868aaf8b05a3fb3703
Source dataset
uspto-grants-1997_12
Patent number
US05702710

Reaction notes

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