HCID 54397734, compound → HCID 9820546, compound

HRID 612734Notes

Reaction equation

HRID 612734 reaction equation
C([O:3][C:4](=[O:29])[CH:5]=[C:6]([CH3:28])[CH:7]=[CH:8][CH2:9][C:10]1([C:13]2[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:19]=[C:18]3[C:14]=2[CH2:15][CH2:16][C:17]3([CH3:27])[CH3:26])[CH2:12][CH2:11]1)C>CO>[C:22]([C:20]1[CH:19]=[C:18]2[C:14]([CH2:15][CH2:16][C:17]2([CH3:27])[CH3:26])=[C:13]([C:10]2([CH2:9]/[CH:8]=[CH:7]/[C:6](/[CH3:28])=[CH:5]/[C:4]([OH:29])=[O:3])[CH2:11][CH2:12]2)[CH:21]=1)([CH3:23])([CH3:24])[CH3:25]

Participants

3

Reactant 1

HCID 54397734HCID 54397734, compound

Product 1

HCID 9820546HCID 9820546, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The above ethyl ester 19 (37 mg, 0.09 mmol) in 2 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 18 mg (55%) of pure (2E, 4E)-6-[1-(6-t-butyl-1,1-dimethyl-indan-4-yl)-cyclopropyl]-3-methyl-2,4-hexadienoic acid (20). 1H NMR (400 MHz, CDCl3) δ7.05 (d, J=1.5 Hz, 1H, aromatic), 7.02 (d, J=1.7 Hz, 1H, aromatic), 6.09 (dt, J=15.7 and 7.2 Hz, 1H, vinylic CH), 5.97 (d, J=15.7 Hz, 1H, vinylic CH), 5.66 (s, 1H, vinylic CH), 2.90 (t, J=7.2 Hz, 2H, allylic CH2), 2.34 (d, J=7.2 Hz, 2H, allylic CH2), 2.22 (s, 3H, aliphatic CH3), 1.91 (t, J=7.0 Hz, 2H, aliphatic CH2), 1.30 (s, 9H, aliphatic 3CH3), 1.25 (s, 6H, aliphatic 2CH3), 0.80 (dd, J=10.1, 6.2 Hz, 2H, aliphatic CH2), 0.71 (dd, J=10.2, 3.9 Hz, 2H, aliphatic CH2).

Workup

  1. customto give the crude acid

Sources & evidence

ORD record
ord-849277df2c424088a58ddca9a1b994da
Source dataset
uspto-grants-1999_12
Patent number
US06005007

Reaction notes

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