3,4-dihydro-2H-pyran → HCID 54004954, compound

HRID 2255146Notes

Reaction equation

HRID 2255146 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.[OH:19][N:20]=[C:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22]([OH:24])=[O:23].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:19][N:20]=[C:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22]([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 573586802-(Hydroxyimino)-4-methylpentanoic acid

Product 1

HCID 54004954HCID 54004954, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.6 Milliliters of 3,4-dihydro-2H-pyran and 0.29 g of p-TsOH.H2O were added to 50 ml of a solution of 4.35 g of α-hydroxyimino-isocaproic acid dissolved in dry CH2Cl2. The mixture was stirred for 100 minutes at room temperature. The reaction mixture was added to an aqueous solution saturated with NaHCO3 with ice cooling, and subjected to phase separation. An aqueous solution saturated with NaHCO3 was covered with ethyl acetate, then concentrated hydrochloric acid was added thereto, with stirring under ice cooling, to make the reaction mixture weakly acidic. The ethyl acetate layer was separated, washed with an aqueous selection saturated with NaCl, and dried over magnesium sulfate to obtain 6.00 g (87%) of the title compound as a colorless oily substance.

Workup

  1. customsubjected to phase separation
  2. additionconcentrated hydrochloric acid was added
  3. stirringwith stirring under ice cooling
  4. customThe ethyl acetate layer was separated
  5. washwashed with an aqueous selection saturated with NaCl
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-ef0669a73ca44d8ba51457408f5bb6d8
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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