tert-Butanol → tert-Butyl 10-(3-chloro-2,6-dihydroxy-5-formyl-4-methylphenyl)decanoate

HRID 59632Notes

Reaction equation

HRID 59632 reaction equation
C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[Cl:14][C:15]1[C:16]([OH:37])=[C:17]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:18]([OH:24])=[C:19]([CH:22]=[O:23])[C:20]=1[CH3:21].[CH3:38][C:39](O)([CH3:41])[CH3:40].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[C:16]([OH:37])=[C:17]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][C:39]([CH3:41])([CH3:40])[CH3:38])=[O:35])[C:18]([OH:24])=[C:19]([CH:22]=[O:23])[C:20]=1[CH3:21]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 8670133710-(3-Chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)decanoic acid

Product 1

HCID 86701336tert-Butyl 10-(3-chloro-2,6-dihydroxy-5-formyl-4-methylphenyl)decanoateYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

TFAA (0.20 ml, 1.4 mmol) was added to a suspension of Compound 215-11-COOH (144 mg, 0.403 mmol) in toluene (5 ml) at 0° C., and the mixture was allowed to warm to room temperature with stirring for 30 minutes. After checking for complete dissolution of the raw material, the mixture was again cooled to 0° C. tBuOH (0.40 ml, 4.2 mmol) was added to the cooled mixture, which was allowed to warm to room temperature with stirring for 15 hours. A saturated aqueous NaHCO3 solution was added to the reaction solution, which was extracted with EtOAc twice after stirring for 5 minutes. The combined organic layer was washed with a saturated aqueous NaCl solution, and was dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc=7:1 to 4:1) followed by PTLC (Hexane:EtOAc=7:1) to yield the target product (28 mg, 17%).

Workup

  1. additionwas added to the cooled mixture, which
  2. temperatureto warm to room temperature
  3. stirringwith stirring for 15 hours
  4. extractionwas extracted with EtOAc twice
  5. stirringafter stirring for 5 minutes
  6. washThe combined organic layer was washed with a saturated aqueous NaCl solution
  7. dry with materialwas dried over anhydrous Na2SO4
  8. customAfter evaporation of the solvent
  9. customthe residue was purified by column chromatography on silica gel (Hexane:EtOAc=7:1 to 4:1)

Sources & evidence

ORD record
ord-c417d92c592d4fa59c0ee801cef0a675
Source dataset
uspto-grants-2016_09
Patent number
US09440913B2

Reaction notes

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