HCID 15735939, compound → Methyl 5-(4-hydroxybutyl)thiophene-2-carboxylate

HRID 889072Notes

Reaction equation

HRID 889072 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]#[C:11][CH2:12][CH2:13][OH:14])=[CH:8][CH:9]=1)=[O:4]>[Pd].CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 15735939HCID 15735939, compound

Product 1

HCID 14796144Methyl 5-(4-hydroxybutyl)thiophene-2-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a Parr flask were added 2 (1.17 g, 5.6 mmol), 10% palladium on activated carbon (600 mg), and MeOH (100 mL). Hydrogenation was carried out at 55 psi of H2 for 4 h. The reaction mixture was filtered through Celite, washed with MeOH (100 mL) and concentrated under reduced pressure to give 1.14 g of 3 as yellow oil. 1H NMR (DMSO-d6): δ 1.41-1.48 (m, 2H), 1.61-1.68 (m, 2H), 2.81-2.85 (t, J=7.2 Hz, 2H), 3.37-3.42 (m, 2H), 3.77 (s, 3H), 4.40-4.43 (t, J=5.2 Hz, 1H), 6.94-6.95 (d, J=3.6 Hz, 1H), 7.63-7.64 (d, J=3.6 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with MeOH (100 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40c015a565ca48ea94105bdde1f1916a
Source dataset
uspto-grants-2012_08
Patent number
US08252804B2

Reaction notes

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