Water → HCID 14621467, compound

HRID 1651668Notes

Reaction equation

HRID 1651668 reaction equation
[O:1]([CH2:9][C@H:10]1[C@@H:15]([CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:14][O:13][C@@H:12]([CH3:25])[O:11]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C:26](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[O:1]([CH2:9][C@H:10]1[C@@H:15]([CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:26])=[O:23])[CH2:14][O:13][C@@H:12]([CH3:25])[O:11]1)[Si:2]([C:5]([CH3:8])([CH3:6])[CH3:7])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14621465HCID 14621465, compound

Product 1

HCID 14621467HCID 14621467, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2R,4R,5S)-4-t-butyldimethylsiloxymethyl-5-[(Z)-6-carboxy-2-hexenyl]-2-methyl-1,3-dioxane (4.75 g) in N,N-dimethylformamide (50 ml) were added potassium carbonate (1.76 g) and methyl iodide (1.62 ml) and the mixture was stirred at room temperature for 5 hours. The solution was poured into water and the resulting aqueous solution was extracted with ether. The organic layer was washed successively with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column (75 g) with a mixture of n-hexane and ethyl acetate (20:1) as an eluent to give (2R,4R,5S) -4-t-butyldimethylsiloxymethyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (4.17 g) as an oil.

Workup

  1. extractionthe resulting aqueous solution was extracted with ether
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was chromatographed on a silica gel column (75 g) with a mixture of n-hexane and ethyl acetate (20:1) as an eluent

Sources & evidence

ORD record
ord-124a0704dd834a2a880a0e370079b84c
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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