HCID 53989278, compound → HCID 9884959, compound

HRID 612731Notes

Reaction equation

HRID 612731 reaction equation
C([O:3][C:4](=[O:28])[CH:5]=[C:6]([CH3:27])[CH:7]=[CH:8][CH2:9][C:10]1([C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=2)[CH2:12][CH2:11]1)C>CO>[C:23]([C:15]1[CH:14]=[C:13]([C:10]2([CH2:9]/[CH:8]=[CH:7]/[C:6](/[CH3:27])=[CH:5]/[C:4]([OH:28])=[O:3])[CH2:11][CH2:12]2)[CH:18]=[C:17]([C:19]([CH3:21])([CH3:22])[CH3:20])[CH:16]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

3

Reactant 1

HCID 53989278HCID 53989278, compound

Product 1

HCID 9884959HCID 9884959, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The above ethyl ester 11 (712 mg, 2.18 mmol) in 35 mL MeOH was hydrolyzed as described for Example 1 to give the crude acid. The crude mixture was purified by HPLC (80% MeOH/20% 10 mmol NH4OAc+0.3% AcOH) to give 390 mg (60%) of pure (2E, 4E)-6-[1-(3,4-diethylbenzene)-cyclopropyl]-3-methyl-2,4-hexadienoic acid (12). 1H NMR (400 MHz, CDCl3) δ7.04 (m, 3H, aromatic), 6.15 (dt, J=15.6 and 6.8 Hz, 1H, vinylic CH), 6.05 (d, J=15.6 Hz, 1H, vinylic CH), 5.69 (s, 1H, vinylic CH), 2.62 (q, J=7.5 Hz, 4H, aliphatic 2CH2), 2.43 (d, J=6.8 Hz, 2H, allylic CH2), 2.23 (s, 3H, aliphatic CH3), 1.20 (m, 6H, aliphatic 2CH3), 0.84 (dd, J=6.2, 4.7 Hz, 2H, aliphatic CH2), 0.73 (dd, J=5.4, 4.1 Hz, 2H, aliphatic CH2).

Workup

  1. customto give the crude acid

Sources & evidence

ORD record
ord-0461d3fff1714ff985d60fa812e855d2
Source dataset
uspto-grants-1999_12
Patent number
US06005007

Reaction notes

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