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

HRID 1676115ノート

反応式

HRID 1676115 の反応式
[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]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 594978694-Isobutyl-3-methylthiophene-2-carboxylic acidHCID 178418348HCID 178418348、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a6a43936a8764ffeb9ea5954e10fad7d
出典データセット
uspto-grants-2011_08
特許番号
US08003800B2

反応ノート

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