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

HRID 2046555ノート

反応式

HRID 2046555 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-708f1d7cb6334aa4a012cc8157bc2c14
出典データセット
uspto-grants-2013_11
特許番号
US08592426B2

反応ノート

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