Dimethylformamide dimethyl acetal → 2-(2-Carbomethoxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

HRID 437487Notes

Reaction equation

HRID 437487 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:10]([C:11]([CH3:13])=[CH2:12])[CH2:9][CH2:8][C:7]=1[CH3:14])([OH:3])=[O:2].[CH3:15]OC(OC)N(C)C>C1C=CC=CC=1>[C:1]([CH2:4][CH2:5][C:6]1[CH:10]([C:11]([CH3:13])=[CH2:12])[CH2:9][CH2:8][C:7]=1[CH3:14])([O:3][CH3:15])=[O:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 213885332-(2-Carboxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

Product 1

HCID 213885312-(2-Carbomethoxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-eneYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2 g of 2-(2-carboxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene, 150 ml of absolute benzene and 4 ml of dimethoxy-dimethylamino-methane was heated for 5 hours to reflux. The solution was concentrated and the residue, obtained as a red oil, chromatographed on 50 g of silicagel with hexane/ether (19:1). There were obtained 1.95 g (91%) of 2-(2-carbomethoxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene; boiling point 0.01 about 70° C; nD20 = 1.4761; IRfilm : νmax = 3100, 1742, 1645, 1440, 1375, 1330, 1255, 1195, 1170, 1085, 1025, 990, 895 and 840 cm-1. The compound has a floral, woody, ester-like fragrance.

Workup

  1. temperaturewas heated for 5 hours
  2. temperatureto reflux
  3. concentrationThe solution was concentrated
  4. customthe residue, obtained as a red oil
  5. customchromatographed on 50 g of silicagel with hexane/ether (19:1)

Sources & evidence

ORD record
ord-62dd1ee966054623845a839c1969763e
Source dataset
uspto-grants-1977_06
Patent number
US04031132

Reaction notes

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