Triethylamine → 1,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoate

HRID 1647075ノート

反応式

HRID 1647075 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19].[CH3:23][C:22]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1)([CH3:25])[CH3:24]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 148887285-(4-bromophenyl)-2-(1,1-dimethylethyl)-2H-tetrazole

生成物 1

HCID 867465281,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoate収率 55%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

A solution of 5-(4-bromophenyl)-2-(1,1-dimethylethyl)-2H-tetrazole (3.0 g, 10.2 mmol), t-butyl acrylate (2.9 mL, 20.4 mmol), and triethylamine (7.9 mL, 59 mmol) in DMF (93 mL) was deoxygenated with argon, whereupon bis(triphenylphosphine)palladium dichloride (0.5 g, 0.8 mmol) was added. After heating at 75° C. for 12 hours the mixture was concentrated under reduced pressure and the brown residue was filtered through a short column of silica gel eluting with a mixture of hexanes and ethyl acetate (9:1). The eluent was concentrated and then purified by chromatography on a Waters Prep 500 liquid chromatograph fitted with two silica gel cartridges eluting with a mixture of hexanes and ethyl acetate (9:1). The fractions containing product were pooled, concentrated and the residue was recrystallized from hexanes to give 1,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoate (1.6 g, 5.6 mmol) in 55% yield, mp. 118.5°-120° C.

後処理

  1. additionwas added
  2. concentrationwas concentrated under reduced pressure
  3. filtrationthe brown residue was filtered through a short column of silica gel eluting with a mixture of hexanes and ethyl acetate (9:1)
  4. concentrationThe eluent was concentrated
  5. custompurified by chromatography on a Waters Prep 500 liquid chromatograph
  6. customfitted with two silica gel cartridges
  7. washeluting with a mixture of hexanes and ethyl acetate (9:1)
  8. additionThe fractions containing product
  9. concentrationconcentrated
  10. customthe residue was recrystallized from hexanes

出典と根拠

ORDレコード
ord-b9d69949f9a84832b3afa54170ed9770
出典データセット
uspto-grants-1993_01
特許番号
US05182263

反応ノート

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