Toluene → HCID 18694138, compound

HRID 1870983Notes

Reaction equation

HRID 1870983 reaction equation
[O:1]1[C:6]2[C:7]3[CH2:13][CH2:12][CH2:11][C:8]=3[CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[C:14](O)=[O:15].C(N1C=CN=C1)(N1C=CN=C1)=O.[H-].C([Al+]CC(C)C)C(C)C.CC1C=CC=CC=1>O1CCCC1.O.CO>[O:1]1[C:6]2[C:7]3[CH2:13][CH2:12][CH2:11][C:8]=3[CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH:14]=[O:15]

Participants

8

Reactant 4

HCID 1140TolueneHCID 682631,1'-CarbonyldiimidazoleHCID 18694185HCID 18694185, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18694138HCID 18694138, compoundYield 53.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

A mixture of intermediate (4-a) (0.11 mol) in tetrahydrofuran (250 ml) was stirred under nitrogen flow. 1,1'-Carbonylbis-1H-imidazole (0.11 mol) was added and the reaction mixture was stirred for 2 hours at room temperature. Then, it was cooled to -80° C. A solution of diisobutylaluminum hydride in methylbenzene (20%) (0.33 mol) was added dropwise and the reaction mixture was stirred for 2 hours at -80° C. The mixture was decomposed with methanol, then poured out into water. The mixture was acidified, then extracted with 1,1'-oxybisethane. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated, yielding 12 g of (±)-2,3,4,7,8,9-hexahydrocyclopenta[h]-1-benzopyran-2-carboxaldehyde (interm. 5-a).

Workup

  1. stirringthe reaction mixture was stirred for 2 hours at room temperature
  2. stirringthe reaction mixture was stirred for 2 hours at -80° C
  3. extractionextracted with 1,1'-oxybisethane
  4. dry with materialThe separated organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8f716151756745b1a7f32e52362b6af2
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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