Methyl iodide → Methyl 5-bromo-1-methyl-2,3-dihydro-1H-indene-1-carboxylate

HRID 2046555노트

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HRID 2046555 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]([CH:15]1[C:23]2[C:18](=[CH:19][C:20]([Br:24])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)=[O:14].I[CH3:26]>C1COCC1>[CH3:11][O:12][C:13]([C:15]1([CH3:26])[C:23]2[C:18](=[CH:19][C:20]([Br:24])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)=[O:14]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 13840001Methyl 5-bromo-2,3-dihydro-1H-indene-1-carboxylate

생성물 1

HCID 57419486Methyl 5-bromo-1-methyl-2,3-dihydro-1H-indene-1-carboxylate수율 95.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

Lithium bis(trimethylsilyl)amide (6.16 ml, 6.16 mmol, 1M solution in THF) was added dropwise to a solution of (rac)-5-bromo-indan-1-carboxylic acid methyl ester (1.31 g, 5.14 mmol) in dry THF (25 ml) at −78° C. After the addition was completed, the solution was stirred at −78° C. for 45 minutes. Then, iodomethane (2.19 g, 959 μl, 15.4 mmol) was added, the solution was allowed to warm to room temperature and stirred for 48 h. The reaction was quenched by addition of sat. NH4Cl solution and extracted two times with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4 and evaporated. The remaining yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5) to obtain the title compound as yellow oil (1.319 g, 95%). MS: 269.2 [M+H]+.

후처리

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. stirringstirred for 48 h
  4. customThe reaction was quenched by addition of sat. NH4Cl solution
  5. extractionextracted two times with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried with Na2SO4
  8. customevaporated
  9. customThe remaining yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5)

출처 및 근거

ORD 기록
ord-708f1d7cb6334aa4a012cc8157bc2c14
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592426B2

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