Sodium Phosphate, Dibasic → HCID 57004359, compound

HRID 613446Notes

Reaction equation

HRID 613446 reaction equation
Cl[O-:2].[Na+].P([O-])([O-])(O)=O.[Na+].[Na+].[CH2:11]([O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[O:22][C:21]([CH3:27])([CH3:26])[CH:20]=[CH:19]2)[CH2:12][CH2:13][CH3:14]>C(Cl)Cl>[CH2:11]([O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[O:22][C:21]([CH3:26])([CH3:27])[C@H:20]1[O:2][C@@H:19]21)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 10998881HCID 10998881, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 57004359HCID 57004359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S, 4S)-(-)-6-Butoxy-2,2-dimethyl-3,4-epoxychroman At 0° C., 76 ml (42 mmol) of a 0.55 M sodium hypochlorite solution which had been adjusted to pH 11.3 using disodium hydrogen phosphate were added to a solution of 4.6 g (20 mmol) of 6-butoxy-2,2-dimethyl-2H-chromen (Example 5b) and 0.5 g (0.8 mmol) of (S,S)-(+)-N,N'-bis-(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexanemanganese(III) chloride (Jacobsen's catalyst) in 20 ml of methylene chloride. The reaction mixture was stirred vigorously for 3 h and the organic phase was then separated off and the aqueous phase was extracted twice with methylene chloride. Silica gel chromatography of the crude product using cyclohexane/EA 9:1 gave 1.6 g of (3S, 4S)-(-)-6-butoxy-2,2-dimethyl-3,4-epoxychroman; optical rotation -14.9° (c=0.6; methanol).

Workup

  1. customthe organic phase was then separated off
  2. extractionthe aqueous phase was extracted twice with methylene chloride

Sources & evidence

ORD record
ord-905ac815f07541ad84a604aa35cd5f55
Source dataset
uspto-grants-1999_12
Patent number
US06008245

Reaction notes

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