4-(4-Hydroxy-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester → 4-(4-Hydroxy-butyl)-thiophene-2-carboxylic acid methyl ester

HRID 2074038Notes

Reaction equation

HRID 2074038 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[S:9][CH:10]=1.[H][H]>C(O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[S:9][CH:10]=1

Participants

5

Reactant 2

HCID 147961434-(4-Hydroxy-but-1-ynyl)-thiophene-2-carboxylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 147961424-(4-Hydroxy-butyl)-thiophene-2-carboxylic acid methyl esterYield 81.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr flask was charged with 4.00 g of methyl 4-(4-hydroxybut-1-yn-1-yl)thien-2-ylcarboxylate in 100 mL of ethanol. Then 2.00 g (50% wt eq) of 5% palladium on charcoal was added. Parr hydrogenation was carried out at 50 psi of hydrogen for 6 hours. The reaction mixture was filtered through a Celite pad which was washed with ethanol. The filtrate was concentrated under reduced pressure to give 3.34 g (81.9%) of methyl 4-(4-hydroxybutyl)thien-2-ylcarboxylate as a clear oil; IR (KBr, cm-1): 1710, 1444, 1293, 1260, 1225; UV (Ethanol) :λmax =281 nm (epsilon=6450), 248 nm (epsilon=10,100); 1H NMR (CDCl3, 300 MHz) delta 7.59 (s, 1H), 7.12, (s, 1H), 3.81 (s, 3H), 3.60 (t, J=6.3 Hz, 2H), 2.59 (t, J=7.4 Hz, 2H), 2.10 (bs, 1H), 1.60-1.68 (m, 2H), 1.51-1.58 (m, 2H); MASS: M+ =2148 (EICEC).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad which
  2. washwas washed with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-364bfcf1a17245278844297a6b0e992d
Source dataset
uspto-grants-1990_04
Patent number
US04920125

Reaction notes

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