Water → HCID 53835364, compound

HRID 437495Notes

Reaction equation

HRID 437495 reaction equation
[CH3:1][Li].[CH:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1.BrC[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].O>O1CCCC1>[C:15]([CH:14]([CH2:13][CH2:12][CH2:11][CH3:10])[CH2:1][C:4]1[CH:3]=[CH:7][CH:6]=[C:5]=1)([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7612CyclopentadieneHCID 122490Ethyl 7-bromoheptanoateHCID 178418348HCID 178418348, compound

Product 1

HCID 53835364HCID 53835364, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of CH3Li(1.95 M, 0.65 mole, 333 ml.) was added under nitrogen to a magnetically stirred solution of freshly distilled cyclopentadiene (60 ml., 0.68 mole) in dry tetrahydrofuran (THF) (550 ml.) with ice bath cooling. To this resulting white suspension ethyl 7-bromoheptanoate (120 g., 0.54 mole) was added dropwise over a period of 1/2 hour. The mixture was allowed to warm to room temperature and stirred for 3 hours. The resulting clear solution was poured into water and extracted with ether (3 l). The extract was washed twice with water, once with saturated brine, dried (MgSO4) and evaporated at room temperature. This process gave almost pure 2-carboethoxyhexyl-2-cyclopentene-1,4-diene (I).

Workup

  1. temperaturecooling
  2. extractionextracted with ether (3 l)
  3. washThe extract was washed twice with water, once with saturated brine
  4. dry with materialdried (MgSO4)
  5. customevaporated at room temperature

Sources & evidence

ORD record
ord-123f7d7b37ee49ed88b4f195686aab02
Source dataset
uspto-grants-1977_06
Patent number
US04031129

Reaction notes

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