Dimethylformamide → HCID 15042010, compound

HRID 2371502Notes

Reaction equation

HRID 2371502 reaction equation
I[CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]1.[C:19]([C:23]1[CH:28]=[C:27]([SH:29])[CH:26]=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]=1[OH:34])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.C(Cl)Cl>[C:30]([C:25]1[CH:26]=[C:27]([S:29][CH2:2][C@H:3]2[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]2)[CH:28]=[C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:24]=1[OH:34])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 15042006HCID 15042006, compound

Product 1

HCID 15042010HCID 15042010, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A mixture of 0.12 g (0.324 mmol) of tert-butyl [(4R,6S)-6-(iodomethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate, 0.0925 g (0.388 mmol) of 2,6-di-tert-butyl-4-mercaptophenol (See R. J. Laufer, U.S. Pat. No. 3,129,262), 0.067 g (0.49 mmol) of powderly anhydrous potassium carbonate and 0.5 ml of dry N,N-dimethylformamide was stirred for 16 hours at room temperature. The reaction solution was distilled away under reduced pressure. The residue was dissolved in ether, washed with saturated brine solution, dried and distilled away under reduced pressure. The residue was purified by subjecting to silica gel column chromatography [eluent: ethyl acetate-methylene chloride (1:19)]]to give 0.143 g of tert-butyl [(4R,6S)-6-[[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]methyl]-2,2-dimethyl-1,3-dioxane-4-yl]acetate as crystals (yield: 92%). The desired compound was recrystallized from hexane.

Workup

  1. distillationThe reaction solution was distilled away under reduced pressure
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with saturated brine solution
  4. customdried
  5. distillationdistilled away under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-102a3e87c397448f949eef25e1d83f84
Source dataset
uspto-grants-1992_03
Patent number
US05093363

Reaction notes

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