Cornforth reagent → HCID 11126991, compound

HRID 1612813Notes

Reaction equation

HRID 1612813 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 0.1M 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) δ3.59 (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-7173a3b6d6bb46679b4bbeeb26752bdb
Source dataset
uspto-grants-1993_03
Patent number
US05190969

Reaction notes

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