Ethanol → HCID 54117635, compound

HRID 1637104Notes

Reaction equation

HRID 1637104 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.[CH3:28][CH2:29]O>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)[CH3:29]

Participants

4

Reactant 2

HCID 702EthanolHCID 15463366HCID 15463366, compound

Product 1

HCID 54117635HCID 54117635, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylethynylpropionic acid (250 mg, 0.69 mmol) in EtOH (20 ml) and H2SO4 (1 drop) was refluxed for 6 hr. The solvent was evaporated, the residue taken up in Et2O, washed with aqueous Na2CO3, dried, and the solvent evaporated. The residue was crystallized from hexane, and gave the titled compound, 180 mg (67%). 1H NMR (400 MHz, CDCl3) δ 7.40 (m, 2 H), 7.28 (m, 3 H), 6.98 (m, 2 H), 6.82 (d, 1 H), 4.80 (m, 1 H), 4.32 (t, 1 H), 4.14 (q, 2 H), 3.80 (s, 3 H), 2.86 (d of d, 1 H), 2.76 (d of d, 1 H), 1.76-1.98 (m, 6 H), 1.62 (m, 2 H), 1.22 (t, 3 H).

Workup

  1. customThe solvent was evaporated
  2. washwashed with aqueous Na2CO3
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-fbab118fefb34f2bbcd1acf1ef12826b
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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