Tetrahydrofuran → HCID 59516956, compound

HRID 2079112Notes

Reaction equation

HRID 2079112 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-b2d2a94bae18404ba73bbbd0451e7161
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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