Cornforth reagent → HCID 13429748, compound

HRID 1858899Notes

Reaction equation

HRID 1858899 reaction equation
[CH2:1]([C@@H:8]1[O:10][C@@H:9]1[CH2:11][OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:14].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C=O)C.O.Cl>[CH2:1]([C@H:8]1[O:10][C@H:9]1[C:11]([OH:14])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 2

HCID 2724130Cornforth reagentHCID 3000234123932-68-3

Product 1

HCID 13429748HCID 13429748, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 300 mg (1.16 mmole) (2R-cis)-3-heptyloxiranemethanol in 50 ml of DMF was added 2.62 g (6.97 mmole) of pyridinium dichromate. The reaction was allowed to stir overnight under argon. The mixture was then diluted with 150 ml H2O and 20 ml 0.1 M HCl and washed three times with 50 ml of Et2O. The combined Et2O layers are dried over MgSO4, filtered and evaporated to afford a white powder. This residue was crystallized from petroleum ether to afford 155 mg of white power, mp 53-5° C. 1H NMR (CDCl3) δ 3.60 (d, 1, J=5 Hz), 3.24 (dd, 1, J=5 12 Hz), 1.6-1.2 (m, 12), 0.88 (t, 3, J=7 Hz). Mass Spectra: M-45(--CO2H)(3.7)141.1, M(100)41.0.

Workup

  1. washwashed three times with 50 ml of Et2O
  2. dry with materialThe combined Et2O layers are dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a white powder
  6. customThis residue was crystallized from petroleum ether
  7. customto afford 155 mg of white power, mp 53-5° C

Sources & evidence

ORD record
ord-36b12bd304ad4635aa445f20c55362a7
Source dataset
uspto-grants-2000_11
Patent number
US06153589

Reaction notes

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