Acetic Anhydride → Ethyl ethoxymethyleneacetoacetate

HRID 542524노트

반응식

HRID 542524 반응식
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH:10](OCC)(OCC)[O:11][CH2:12][CH3:13].C(OC(=O)C)(=O)C>>[CH2:12]([O:11][CH:10]=[CH:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 8868Ethyl AcetoacetateHCID 31214Ethyl orthoformate

생성물 1

HCID 54463595Ethyl ethoxymethyleneacetoacetate수율 70%

실험 절차

Using the procedure of Crombie et al., Journ. of Chem. Soc. Perkin Trans. 1, 464-471 (1979), a solution of ethyl acetoacetate (26 g, 0.20 mol), triethyl orthoformate (29.6 g, 0.20 mol) and acetic anhydride (41 g, 0.40 mol) was refluxed for 90 minutes. Distillation under reduced pressure gave the product (1): 26 g, 70% yield; bp=85°-98° C. at 0.5 mm Hg (The following value is reported in the Crombie et al. publication: bp=85° C. at 0.25 mm Hg); NMR (CDCl3) δ 1.2-1.5 (m, 6H), 2.4-2.5 (d,3H), 4.0-4.6 (m,4H), 7.7 (d,1H). The signals were split into pairs of closely spaced lines indicative of the cis and trans isomers.

후처리

  1. distillationDistillation under reduced pressure

출처 및 근거

ORD 기록
ord-b2a160b50ff64893a2277996949e7953
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04657919

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