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

HRID 661163

반응식

HRID 661163 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 11070524Ethyl 2-(4-methylphenyl)propanoate수율 86%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

실험 절차

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, 2H, J=8.1), 7.10 (d, 2H, J=8.1), 4.09 (m, 2H), 3.67 (q, 1H, J=7.2), 2.29 (s, 3H), 1.47 (d, J=7.2 Hz, 3H), 1.20 (t, J=5.7 Hz, 3H). 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.

후처리

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

출처 및 근거

ORD 기록
ord-b4ccab7bce8e4c68ad27efe260e8b3d3
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084498B2

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