Tetrahydrofuran → HCID 66809280, compound

HRID 883464Notes

Reaction equation

HRID 883464 reaction equation
N1C=CC=C1[C:6]1[CH2:12][CH2:11][CH2:10][CH:9]=[C:8]([C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])[C:7]=1[C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21].O1CCCC1>O>[C:8]1([C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])[C:7]([C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])=[CH:6][CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 66809308HCID 66809308, compound

Product 1

HCID 66809280HCID 66809280, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a four-necked two litter flask purged with nitrogen, 165.4 g (455.0 mmol) of diisobutyl 3-pyrrolylcyclohepta-2,7-diene-1,2-dicarboxylate obtained in Reference Example 2 and 1,158 mL of tetrahydrofuran were charged. Thereto, 500.0 mL (containing 455.0 mmol of borane-tetrahydrofuran complex) of a tetrahydrofuran solution (concentration: 0.91M) of a borane-tetrahydrofuran complex was added dropwise over 1.5 hour. The mixture was stirred for 6 hours at room temperature. The reaction mixture was provided with water, and the resultant mixture was subjected to toluene extraction. The extraction liquid was washed with water, and was dried over anhydrous magnesium sulfate. The dried liquid was filtered, and volatile matters contained therein were distilled away under reduced pressure to obtain orange colored oil. The oil was purified with silica-gel column chromatography (developing solvent: mixed solvent of 4 parts by volume of hexane with one part by volume of ethyl acetate), thereby obtaining 105.0 g (yield: 78.0%) of diisobutyl cyclohepta-2,7-diene-1,2-dicarboxylate as pale yellow oil with a purity of 99.6% determined by a gas chromatography measurement, its NMR and GCMS data being shown below:

Workup

  1. additionwere charged
  2. extractionthe resultant mixture was subjected to toluene extraction
  3. extractionThe extraction liquid
  4. washwas washed with water
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationThe dried liquid was filtered
  7. distillationvolatile matters contained therein were distilled away under reduced pressure
  8. customto obtain orange colored oil
  9. customThe oil was purified with silica-gel column chromatography (developing solvent: mixed solvent of 4 parts by volume of hexane with one part by volume of ethyl acetate)

Sources & evidence

ORD record
ord-5d378fb8ecc4440fa92ade2d49138fa8
Source dataset
uspto-grants-2012_08
Patent number
US08236908B2

Reaction notes

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