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

HRID 1721250노트

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HRID 1721250 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31007a98a4f049e6a48498da04004d40
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05508437

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