Cornforth reagent → HCID 11126991, compound

HRID 1858900Notes

Reaction equation

HRID 1858900 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 11126991HCID 11126991, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg (2.50 mmole) of (2R-cis)-3-heptyloxiranemethanol in 50 ml of DMF was added 3.30 g (8.75 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 were dried over MgSO4, filtered and evaporated to afford a white powder. This residue was crystallized from petroleum ether to afford 39 mg of white power, mp 62-3° C. 1H NMR (CDCl3) δ 3.59 (d, 1, J=5 Hz), 3.24 (m, 1), 1.6-1.2 (m, 12), 0.88 (t, 3, J=7 Hz). Mass Spectra: M+(19.1)186.1, M-45(42.3)141.1, M(100)95.1.

Workup

  1. washwashed three times with 50 ml of Et2O
  2. dry with materialThe combined Et2O layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a white powder
  6. customThis residue was crystallized from petroleum ether
  7. customto afford 39 mg of white power, mp 62-3° C

Sources & evidence

ORD record
ord-4e53369c64134a72bf75d38f25ae7b15
Source dataset
uspto-grants-2000_11
Patent number
US06153589

Reaction notes

Loading…