Hydrochloric Acid → HCID 22610217, compound

HRID 1860296Notes

Reaction equation

HRID 1860296 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1([CH3:28])[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[C:19]2[CH2:18][CH:17]([C:25]([OH:27])=[O:26])[CH2:16][C:15]1=2.[CH2:29](I)[CH2:30][CH2:31][CH2:32][CH3:33].Cl>O1CCCC1>[CH3:24][C:20]1([CH3:23])[CH2:21][CH2:22][C:14]([CH3:28])([CH3:13])[C:15]2[CH2:16][C:17]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([C:25]([OH:27])=[O:26])[CH2:18][C:19]1=2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 123351-IodopentaneHCID 22610224HCID 22610224, compoundHCID 178418339Butyllithium

Product 1

HCID 22610217HCID 22610217, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

13.6 g of diisopropylamine were dissolved in 200 ml of THF (tetrahydrofuran) abs. and treated dropwise at −10° with 84 ml of butyl lithium (1.6 molar in hexane). After 15 minutes of stirring at 0° C., a solution of 12 g of 4,4,7,7-tetramethyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid in 40 ml of THF was dropped in. The reaction mixture was stirred for one hour at room temperature, cooled again to 0° C. and treated dropwise with a solution of 26.4 g of pentyl iodide in 30 ml of THF. After stirring for 90 minutes at room temperature, the reaction mixture was poured onto ice/water, acidified with 3N HCl and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and evaporated to yield a pale yellow, partially crystalline oil. Flash chromatography (SiO2, hexane/ethyl acetate=6:1) and crystallization from pentane yielded 12.9 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid as white crystals, m.p. 57-58° C.

Workup

  1. stirringThe reaction mixture was stirred for one hour at room temperature
  2. temperaturecooled again to 0° C.
  3. stirringAfter stirring for 90 minutes at room temperature
  4. additionthe reaction mixture was poured onto ice/water
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customto yield a pale yellow, partially crystalline oil
  10. customFlash chromatography (SiO2, hexane/ethyl acetate=6:1) and crystallization from pentane

Sources & evidence

ORD record
ord-c5800c2234664a76b3e3cd0e721d534a
Source dataset
uspto-grants-2003_03
Patent number
US06528677B1

Reaction notes

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