Methyl iodide → Ethyl 2-(4-methylphenyl)propanoate

HRID 239073

反応式

HRID 239073 の反応式
[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[C:14]1(C)C=CC(CC(OCC)=O)=CC=1.[Li+].CC([N-]C(C)C)C.CI>C1COCC1.CN1C(=O)N(C)CCC1>[C:10]1([CH3:14])[CH:11]=[CH:12][C:7]([CH:5]([CH3:6])[C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 84175Ethyl p-tolylacetateHCID 99643Benzeneacetic acid, alpha-methyl-, ethyl esterHCID 2724682Lithium diisopropylamide

生成物 1

HCID 11070524Ethyl 2-(4-methylphenyl)propanoate収率 86%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

実験手順

According to the procedure given for the synthesis of 202, ethyl p-tolylacetate (2.72 g, 15.2 mmol) was reacted with LDA (7.6 mL, 15.25 mmol) and methyl iodide (3.03 g, 21.30 mmol) in anhydrous THF (70 mL) and DMPU (1 mL). After aqueous workup and extraction, the residue was distilled in high vacuo to give 203 (2.5 g, 86.0%) as an oil. Bp 59-63° C./0.2 mmHg. 1H NMR (CDCl3): δ (ppm) 7.18 (d, 2 H, J=8.1), 7.10 (d, 2 H, J=8.1), 4.09 (m, 2 H), 3.67 (q, 1 H, J=7.2), 2.29 (s, 3 H), 1.47 (d, J=7.2 Hz, 3 H), 1.20 (t, J=5.7 Hz, 3 H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm) 174.71, 137.80, 136.63, 129.33, 129.14, 127.36, 60.66, 45.18, 21.05, 18.70, 14.15.

後処理

  1. extractionAfter aqueous workup and extraction
  2. distillationthe residue was distilled in high vacuo

出典と根拠

ORDレコード
ord-af776805c1c24e9e8a397dbeb88e47ea
出典データセット
uspto-grants-2014_02
特許番号
US08642653B2

関連ノート

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