Picolyl chloride hydrochloride → HCID 14621508, compound

HRID 1651674Notes

Reaction equation

HRID 1651674 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:8]([CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][O:6][C@@H:5]([CH3:19])[O:4]1.[H-].[Na+].Cl.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29]Cl>CN(C)C=O>[CH3:18][O:17][C:15]([CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][C@H:8]1[CH2:7][O:6][C@@H:5]([CH3:19])[O:4][C@H:3]1[CH2:2][O:1][CH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=1)=[O:16]

Participants

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 14621469HCID 14621469, compound

Product 1

HCID 14621508HCID 14621508, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R,4R,5S)-4-hydroxymethyl-5-[(Z) -6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (272 mg) in N,N-dimethylformamide (10 ml) were added sodium hydride (80 mg, 60% in oil) and 2-picolyl chloride hydrochloride (110 mg) and the mixture was stirred at room temperature overnight. The reaction mixture was quenched with saturated aqueous ammonium chloride and the resulting solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified with preparative thin layer chromatography with ethyl acetate as an eluent to give (2R,4R,5S)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl -4-(2-pyridylmethoxymethyl)-1,3-dioxane (201 mg) as a pale yellow oil.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified with preparative thin layer chromatography with ethyl acetate as an eluent

Sources & evidence

ORD record
ord-0cadf6e930004163bddfef78b5bcc65a
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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