Sodium Phosphate, Dibasic → HCID 86588241, compound

HRID 1814384Notes

Reaction equation

HRID 1814384 reaction equation
[C:1]1(/[CH:11]=[CH:12]\[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.P([O-])([O-])(O)=[O:15].[Na+].[Na+]>C(Cl)Cl>[C:1]1([C@H:11]2[O:15][C@H:12]2[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24203Sodium Phosphate, DibasicHCID 12453334HCID 12453334, compound

Product 1

HCID 86588241HCID 86588241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
6 °C

Procedure

(ref. E. Jacobsen, el al; JACS 1991, 7064.) The (Z)-1-(1-naphthyl)-propene (2.06 g, 0.012 mol) was dissolved in methylene chloride, and (R, R)-Jacobsen's catalyst (0.168 g) was added, then cooled to 6° C., and a bleach solution (10 mL, buffered to pH=11.3 with disodium hydrogen phosphate) was added. After 6 h at 6° C., the layers were separated, and the aqueous layer washed with ether. The combined organic layers were washed with water, then brine, dried over magnesium sulfate, filtered and rotovapped. The crude product was chromatographed on silica using 5% ether/pentane, to give the desired (1R, 2S)-1-(1-naphthyl)-1-propene oxide (0.421 g). NMR (CDCl3) 8.1-7.7 (3H, m), 7.6-7.3 (4H, m), 4.6-4.5 (1H, m), 3.7-3.5 (1H, m), 1.0 (3H, d, J=5.3 Hz).

Workup

  1. customthe layers were separated
  2. washthe aqueous layer washed with ether
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. customThe crude product was chromatographed on silica using 5% ether/pentane

Sources & evidence

ORD record
ord-39c025390e3049ebb2a9f103d830d556
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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