Ammonium Chloride → tert-Butyl 5-ethenyl-1H-indole-1-carboxylate

HRID 252054노트

반응식

HRID 252054 반응식
[Li][CH2:2]CCC.[C:6]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH:22]=O)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:6]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH:22]=[CH2:2])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 11172622tert-Butyl 5-formyl-1H-indole-1-carboxylateHCID 178418339Butyllithium

생성물 1

HCID 66890900tert-Butyl 5-ethenyl-1H-indole-1-carboxylate수율 130.5%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

T a suspension of methyltriphenylphosphonium bromide (8.1 g, 22.7 mmol) in THF (140 mL) at 0° C. was added nBuLi (1.6 M in hexanes, 14.2 mL, 22.7 mmol) dropwise over 10 min. After 20 min of stirring, a solution of the 5-formyl-indole-1-carboxylic acid tert-butyl ester (4.63 g, 14.8 mmol) in THF (20 mL) was introduced slowly over 20 min. The reaction was warmed slowly to room temperature, stirred 30 min. The reaction mixture was poured into saturated ammonium chloride and the separated aqueous phase was extracted with ethylacetate (3×100 mL). The combined organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography (methylene chloride to 1% acetone-methylene chloride) to give 5-vinyl-indole-1-carboxylic acid tert-butyl ester (4.7 g, 100%) or similarly 6-vinyl-indole-1-carboxylic acid tert-butyl ester.

후처리

  1. stirringstirred 30 min
  2. extractionthe separated aqueous phase was extracted with ethylacetate (3×100 mL)
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (methylene chloride to 1% acetone-methylene chloride)

출처 및 근거

ORD 기록
ord-40aa9bff163f4b89bcb9aad58780af5c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868002B2

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