HCID 69760555, compound → HCID 9953506, compound

HRID 1860297Notes

Reaction equation

HRID 1860297 reaction equation
C([O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([C:16]2([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][C:23]3[C:22]([CH3:26])([CH3:25])[CH2:21][CH2:20][C:19]([CH3:28])([CH3:27])[C:18]=3[CH2:17]2)=[O:15])=[CH:9][CH:8]=1)=[O:6])C=C>C1COCC1>[C:5]([C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]([C:16]2([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][C:23]3[C:22]([CH3:25])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:27])([CH3:28])[C:18]=3[CH2:17]2)=[O:15])=[CH:11][CH:12]=1)([OH:6])=[O:4]

Participants

3

Reactant 1

HCID 69760555HCID 69760555, compound

Product 1

HCID 9953506HCID 9953506, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

19.2 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid 4-allyloxycarbonyl-phenyl ester were dissolved in 460 ml of THF. The reaction flask was evacuated and ventilated with argon twice. 4.6 g of tetrakis (triphenylphosphine) palladium were added, followed by 37 g of morpholine. The reaction mixture was stirred for 4 hours at room temperature, poured on 1500 ml of ice/water, acidified with 6N HCl and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and evaporated to yield a yellow solid. Purification by column chromatography (SiO2, hexane/ethyl acetate=1:3) and crystallization from ethyl acetate/hexane afforded 12.9 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid 4-carboxy-phenyl ester, m.p. 156-158° C.

Workup

  1. customThe reaction flask was evacuated
  2. addition4.6 g of tetrakis (triphenylphosphine) palladium were added
  3. additionpoured on 1500 ml of ice/water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto yield a yellow solid
  9. customPurification
  10. customby column chromatography (SiO2, hexane/ethyl acetate=1:3) and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-220c255ff1fa4f28aacaca5bea2f5ae3
Source dataset
uspto-grants-2003_03
Patent number
US06528677B1

Reaction notes

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