Formaldehyde → 2-(4-Methoxycarbonyl-2-nitrophenyl)propanol

HRID 2095230노트

반응식

HRID 2095230 반응식
CO[C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.[CH2:16]=[O:17].C[C:19](C)([O-:21])C.[K+]>CS(C)=O>[CH3:16][O:17][C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:11])[CH2:19][OH:21])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1)=[O:15]

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 21938352Methyl 4-ethyl-3-nitrobenzoateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 684541792-(4-Methoxycarbonyl-2-nitrophenyl)propanol수율 38%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a suspension of 4-ethyl-3-nitrobenzoic acid methyl ester (11d) (10 g, 48 mmol) and paraformaldehyde (1.8 g, 60 mmol) in DMSO (10 mL) was added in portions potassium tert-butoxide (1.46 g, 12 mmol), during which the colour of the reaction mixture was changing from yellow to purple. After stirring for 2.5 hours at room temperature, the reaction mixture was directly applied to the silica gel bed of a chromatography column (100 g silica, 3.5×14 cm) and eluted with hexane/ethyl acetate (EA) (3:1, v/v). The slightly yellow product (4d) was obtained in 38% yield (4.42 g, 18 mmol). Rf=0.24 (hexanes/EtOAc 7:3). 1H NMR (250 MHz, CDCl3) δ 8.36 (d, 1H, arom. H(3)), 8.18 (dd, 1H, arom. H(5)), 7.58 (d, 1H, arom. H(6)), 3.93 (s, 3H, COOCH3), 3.78 (m, 2H, α-CH2), 3.54 (sextet, 1H, β-CH), 1.69 (d, 3H, CH3).

후처리

  1. washeluted with hexane/ethyl acetate (EA) (3:1

출처 및 근거

ORD 기록
ord-e63b3aa471a947daa96ab680cb18d9fb
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445734B2

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