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Triphenylphosphine → 3-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

HRID 2089471
ノート
印刷プレビュー

反応式

HRID 2089471 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2O)=[CH:4][CH:3]=1.[NH:13]1[CH:17]=[C:16]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[N:15]=[CH:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC)=O)=NC(OC)=O>C1COCC1>[CH:21]([O:20][C:18]([C:16]1[N:15]([CH:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=3)[CH2:6][CH2:7][CH2:8]2)[CH:14]=[N:13][CH:17]=1)=[O:19])([CH3:23])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 126949197-Bromo-1,2,3,4-tetrahydronaphthalen-1-olHCID 178459416HCID 178459416、化合物

生成物 1

HCID 591994563-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a suspension of 7-bromo-1,2,3,4-tetrahydro-naphthalen-1-ol (2.5 g, 11.0 mmol) and isopropyl 4-imidazolecarboxylate (1.18 g, 7.66 mmol), which can be prepared as described in Example 1, (2.33 g, 10.98 mmol) in THF (20 mL) at 0° C. is added triphenylphosphine and dimethyl azodicarboxylate (40% wt. in toluene, 4.01 g, 10.98 mmol). After 10 min, the cooling bath is removed and after another 30 min, water is added and the mixture is extracted twice with ethyl acetate. The organic layers are dried over magnesium sulfate, filtered, and concentrated. The resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures) to give 3-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 363.02, 365.02 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.42 (d, J=6.1 Hz, 3 H), 1.44 (d, J=6.3 Hz, 3 H), 1.73-1.84 (m, 1 H), 1.89-1.98 (m, 1 H), 2.26-2.40 (m, 2 H), 2.82-2.91 (m, 1 H), 3.00 (dt, J=17.2, 5.6 Hz, 1 H), 5.27-5.37 (m, 1 H), 6.50 (t, J=5.3 Hz, 1 H), 7.26 (d, J=8.3 Hz, 1 H), 7.32 (d, J=2.1 Hz, 1 H), 7.51 (dd, J=8.3, 2.1 Hz, 1 H), 8.23 (d, J=1.5 Hz, 1 H), 8.50 (d, J=1.0 Hz, 1 H).

後処理

  1. customcan be prepared
  2. customthe cooling bath is removed and after another 30 min
  3. additionwater is added
  4. extractionthe mixture is extracted twice with ethyl acetate
  5. dry with materialThe organic layers are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures)

出典と根拠

ORDレコード
ord-889f6a26606e43ca981a5dcd4273e16b
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436035B2

反応ノート

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