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

HRID 1950713ノート

反応式

HRID 1950713 の反応式
[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]

参加物

3

反応物 2

HCID 21226129Dichloromethane methanolHCID 66824254(E)-methyl 4-styryl-1-naphthoate

生成物 1

HCID 103308541-Naphthalenecarboxylic acid, 4-formyl-, methyl ester収率 80%

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7685f6ae50b14fbaabdc4184ded4840a
出典データセット
uspto-grants-2013_03
特許番号
US08404649B2

反応ノート

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