1-Propanol → HCID 70079575, compound

HRID 1637106Notes

Reaction equation

HRID 1637106 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16][C:17]([OH:19])=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:28](O)[CH2:29][CH3:30]>OS(O)(=O)=O>[CH2:28]([O:18][C:17](=[O:19])[CH2:16][CH:15]([C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1)[C:20]#[C:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 10311-PropanolHCID 15463366HCID 15463366, compound

Product 1

HCID 70079575HCID 70079575, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylethynylpropionic acid (200 mg, 0.55 mmol) in n-propanol (15 ml) and conc. H2SO4 (1 drop) was heated at 95° for 5 hr. The solvents were evaporated, the residue taken up in Et2O, washed with H2O, aqueous K2CO3, dried and the solvent evaporated. The residue was purified by flash chromatography (alumina, neutral, activity 1, Et2O), and gave the titled compound as an oil, 125 mg (56%). 1H NMR (400 MHz, CDCl3) δ 7.40 (m, 2 H), 7.28 (m, 3 H), 6.98 (m, 2 H), 6.84 (d, 1 H), 4.80 (m, 1 H), 4.36 (t, 1 H), 4.06 (t, 2 H), 3.82 (s, 3 H), 2.90 (d of d, 1 H), 2.78 (d of d, 1 H), 1.78-1.96 (m, 6 H), 1.64 (m, 4 H), 0.90 (t, 3 H).

Workup

  1. customThe solvents were evaporated
  2. washwashed with H2O, aqueous K2CO3
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was purified by flash chromatography (alumina, neutral, activity 1, Et2O)

Sources & evidence

ORD record
ord-b2309165bd1d444aa5220872625148ea
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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