Methyl 5-chloro-2-ethynylbenzoate → Methyl 5-chloro-2-ethylbenzoate

HRID 1530315노트

반응식

HRID 1530315 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[CH:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

4

반응물 1

HCID 86672667Methyl 5-chloro-2-ethynylbenzoate

생성물 1

HCID 59382453Methyl 5-chloro-2-ethylbenzoate수율 93.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 5-chloro-2-ethynylbenzoate (5.34 g, 27.44 mmol) in Ethyl acetate (135 ml) was added Pd/C (10%) (50% water, 2.92 g, 1.37 mmol). The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. LCMS indicated the reaction had gone to completion and the mixture was filtered through Celite. The filter cake washed with EtOAc (50 ml) and the filtrate was concentrated under reduced pressure to give 5.12 g (93.9%) of methyl 5-chloro-2-ethylbenzoate as a brown oil which was suitable for use without any further purification. LC-MS 56%, 2.21 min (3 minute LC-MS method), m/z=198.9/200.9, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.84 (d, J=2.3 Hz, 1H), 7.39 (dd, J=8.3, 2.3 Hz, 1H), 7.21 (d, J=8.3 Hz, 1H), 3.90 (s, 3H), 2.94 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H).

후처리

  1. filtrationthe mixture was filtered through Celite
  2. washThe filter cake washed with EtOAc (50 ml)
  3. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-87ea7edb5a0b4a82abcaee6e70f563f6
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090562B2

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