Dichloromethane methanol → 1-Naphthalenecarboxylic acid, 4-formyl-, methyl ester

HRID 1950713노트

반응식

[CH:1](/[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1)=C\C1C=CC=CC=1.C(Cl)Cl.C[OH:27]>>[CH:1]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1)=[O:27]

참가 물질

반응물 2

HCID 21226129Dichloromethane methanol

HCID 66824254(E)-methyl 4-styryl-1-naphthoate

생성물 1

HCID 103308541-Naphthalenecarboxylic acid, 4-formyl-, methyl ester수율 80%

실험 절차

A solution of (E)-methyl 4-styryl-1-naphthoate (Preparation 2, 1.31 g, 2.0 mmol) in 3:1 CH2Cl2/MeOH (40 mL) was cooled to −78° C. Sample was subjected to ozonylysis for 10 minutes until blue color was noted. Reaction was quenched with dimethyl sulfide (400 μL) and allowed to warm to room temperature. The residue was purified by chromatography on silica gel eluting from 100% heptane to 50:50 EtOAc:heptane to afford a solid (0.78 g, 80%). 1H NMR (CDCl3) δ ppm: 10.52 (1H), 9.28 (1H), 8.83 (1H), 8.22 (1H), 8.04 (1H), 7.79-7.70 (2H), 4.08 (3H).

후처리

customReaction
customwas quenched with dimethyl sulfide (400 μL)
customThe residue was purified by chromatography on silica gel eluting from 100% heptane to 50:50 EtOAc

출처 및 근거

ORD 기록: ord-7685f6ae50b14fbaabdc4184ded4840a
출처 데이터셋: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08404649B2

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