Tetrahydrofuran → 2-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-diene

HRID 1953039Notes

Reaction equation

HRID 1953039 reaction equation
[C:1]([C:5]1([Li])[CH:9]=[CH:8][CH:7]=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].O1C[CH2:14][CH2:13][CH2:12]1>>[C:1]([C:5]1[CH:9]=[CH:8][C:7](=[C:13]([CH3:14])[CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 178506706HCID 178506706, compound

Product 1

HCID 146882832-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-diene

Procedure

Into a 200 ml, 3-neck flask, equipped with a reflux condenser, a gas inlet tube and a magnetic stirring bar, was charged, under nitrogen, 2 grams t-butylcyclopentadienyl lithium and 25 ml anhydrous tetrahydrofuran (THF). The solution was cooled in an ice-bath and 10 ml acetone, dried over 3A, was cautiously added. The reaction mixture was allowed stir overnight and quenched, cautiously, with 60 ml water. The resulting solution was extracted with ethyl ether using the standard lab extraction procedure. The resulting yellow oil was distilled under vacuum at 40-45° C. to obtain a clear yellow oil, 0.76 g.

Workup

  1. customInto a 200 ml, 3-neck flask, equipped with a reflux condenser, a gas inlet tube and a magnetic stirring bar
  2. additionwas charged, under nitrogen
  3. temperatureThe solution was cooled in an ice-bath
  4. dry with material10 ml acetone, dried over 3A
  5. additionwas cautiously added
  6. customquenched
  7. extractionThe resulting solution was extracted with ethyl ether using
  8. extractionthe standard lab extraction procedure
  9. distillationThe resulting yellow oil was distilled under vacuum at 40-45° C.
  10. customto obtain a clear yellow oil, 0.76 g

Sources & evidence

ORD record
ord-cf34d46bcef94e09909c1a4103b8d0d8
Source dataset
uspto-grants-2000_09
Patent number
US06114480

Reaction notes

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