Pyrrolidine → (+/-)-Methyl 5-oxo-6-((tetrahydrofuran-3-yl)methylene)-5,6,7,8-tetrahydronaphthalene-2-carboxylate

HRID 505704

반응식

HRID 505704 반응식
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2.[O:16]1[CH2:20][CH2:19][CH:18]([CH:21]=O)[CH2:17]1.N1CCCC1.C(OCC)(=O)C.CCCCCC>CO>[O:1]=[C:2]1[C:11](=[CH:21][CH:18]2[CH2:19][CH2:20][O:16][CH2:17]2)[CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2

참가 물질

6

반응물 4

HCID 31268PyrrolidineHCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 15309116Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylateHCID 21226206Ethyl acetate hexane

생성물 1

HCID 66723025(+/-)-Methyl 5-oxo-6-((tetrahydrofuran-3-yl)methylene)-5,6,7,8-tetrahydronaphthalene-2-carboxylate수율 58.2%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
45 °C

실험 절차

To a solution of methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (240 mg, 1.2 mmol) in methanol (3 mL) was added (±)-tetrahydrofuran-3-carboxaldehyde (240 mg, 2.4 mmol) and pyrrolidine (0.20 mL, 2.4 mmol). The solution was stirred for twenty hours at ambient temperature and for four hours at 45° C. The reaction was concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexane) provided (±)-methyl 5-oxo-6-((tetrahydrofuran-3-yl)methylene)-5,6,7,8-tetrahydronaphthalene-2-carboxylate as an orange oil (200 mg, 58% yield). LC/MS on 4.6×50 mm C-18 column, tR=2.52 minutes (10 to 90% acetonitrile/water over 4 minutes at 4 mL/minute with detection 254 nm, at 50° C.); ES-MS m/z 287 (M+H).

후처리

  1. concentrationThe reaction was concentrated in vacuo

출처 및 근거

ORD 기록
ord-2f266235f3e641049e3a9e320e8f7cf7
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781428B2

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