Ammonium Chloride → 1-(4-Isobutyl-3-methylthiophen-2-yl)ethanone

HRID 1676115Notes

Reaction equation

HRID 1676115 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:13])=[C:7]([C:10]([OH:12])=O)[S:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3].[CH3:14][Li].[NH4+].[Cl-]>C(OCC)C>[CH2:1]([C:5]1[C:6]([CH3:13])=[C:7]([C:10](=[O:12])[CH3:14])[S:8][CH:9]=1)[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 594978694-Isobutyl-3-methylthiophene-2-carboxylic acidHCID 178418348HCID 178418348, compound2×

Product 1

HCID 673512221-(4-Isobutyl-3-methylthiophen-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-isobutyl-3-methyl-thiophene-2-carboxylic acid (2.44 g, 12.3 mmol) in diethyl ether (50 mL), a solution of methyllithium (23.1 mL, 1.6 M solution in diethyl ether) is slowly added at 20-23° C. The resulting suspension is stirred at rt for 30 min before another portion of methyllithium (2.3 mL) is added. Stirring is continued for further 30 min before the mixture is poured into vigorously stirred 1 N. aq. NH4Cl (400 mL). The organic phase is separated and the aq. phase is extracted again with diethyl ether. The combined organic extracts are dried over Na2SO4, filtered and evaporated to leave 1-(4-isobutyl-3-methyl-thiophen-2-yl)ethanone (2.34 g) as pale yellow oil; LC-MS: tR=1.03 min, [M+1]=197.20; 1H NMR (CDCl3): δ7.08 (s, 1H), 2.52 (s, 3H), 2.46 (s, 3H), 2.42 (d, J=7.0 Hz, 2H), 1.82 (m, J=7.0 Hz, 1H), 0.92 (d, J=6.4 Hz, 6H).

Workup

  1. additionis added
  2. additionis poured into vigorously stirred 1 N
  3. customThe organic phase is separated
  4. extractionthe aq. phase is extracted again with diethyl ether
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a6a43936a8764ffeb9ea5954e10fad7d
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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