Tetrahydrofuran → HCID 59516956, compound

HRID 1698630Notes

Reaction equation

HRID 1698630 reaction equation
C1COCC1.C[O:7][C:8](=O)[C:9]1[CH:18]=[C:17]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:16]=[C:11]([C:12](OC)=[O:13])[CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[OH:13][CH2:12][C:11]1[CH:10]=[C:9]([CH2:8][OH:7])[CH:18]=[C:17]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:23])[CH3:22])[CH:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59516987HCID 59516987, compound

Product 1

HCID 59516956HCID 59516956, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 ml THF solution containing 21.53 g of 5-triisopropylsilanyloxyisophthalic acid dimethyl ester there was added 7.1 g of lithium aluminum hydride at 0° C. After stirring at 0° C. for 1 hour, the mixture was stirred at room temperature for 3 hours and 30 minutes. Water and 1N aqueous sodium hydroxide were added to the reaction mixture which was then filtered through celite. The filtrate was extracted with ethyl acetate. The organic layer was then washed with saturated brine and dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (13.53 g) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours and 30 minutes
  2. filtrationwas then filtered through celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe organic layer was then washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe desiccating agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-df0ca053594d4eab9605ffe07a9106a6
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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