Water → HCID 53835364, compound

HRID 371906Notes

Reaction equation

HRID 371906 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 one-half 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 1). The extract was washed twice with water, one 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 1)
  3. washThe extract was washed twice with water, one with saturated brine
  4. dry with materialdried (MgSO4)
  5. customevaporated at room temperature

Sources & evidence

ORD record
ord-3034432fb3e944509b8440c65a29c9bf
Source dataset
uspto-grants-1978_05
Patent number
US04088536

Reaction notes

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