HCID 53989278, compound → HCID 9884959, compound

HRID 612728Notes

Reaction equation

HRID 612728 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 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The above ethyl ester 11 (33 mg, 0.09 mmol) in 1.5 mL MeOH was hydrolyzed as described for Example 1 to give the crude acid. The crude mixture was purified by HPLC (82% MeOH/18% 10 mmol NH4OAc+0.3% AcOH) to give 14 mg (45%) of pure (2E, 4E)-6-[1-(3,5-di-t-butyl phenyl)-cyclopropyl]-3-methyl-2,4-hexadienoic acid (12). 1H NMR (400 MHz, CDCl3) δ7.24 (d, J=2.8 Hz, 1H, aromatic), 7.10 (d, J=1.8 Hz, 2H, aromatic), 6.17 (dt, J=15.6 and 7.0 Hz, 1H, vinylic CH), 6.03 (d, J=15.6 Hz, 1H, vinylic CH), 5.68 (s, 1H, vinylic CH), 2.41 (d, J=7.0 Hz, 2H, allylic CH2), 2.24 (s, 3H, aliphatic CH3), 1.31 (s, 18H, aliphatic 6CH3), 0.88 (dd, J=11.2, 7.1 Hz, 2H, aliphatic CH2), 0.74 (dd, J=10.2, 4.1 Hz, 2H, aliphatic CH2).

Workup

  1. customto give the crude acid

Sources & evidence

ORD record
ord-2480265e138740cc9281af1b260a2762
Source dataset
uspto-grants-1999_12
Patent number
US06005007

Reaction notes

Loading…