Chlorotrimethylsilane → HCID 15434957、化合物

HRID 2185031ノート

反応式

HRID 2185031 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si](Cl)(C)C.[CH2:16]([C:19]1[CH:40]=[C:39]([O:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:38]=[CH:37][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:28][CH:27]=1)[CH2:17][CH3:18].[Br:48]N1C(=O)CCC1=O>C1COCC1>[Br:48][CH:32]([C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][CH2:22][O:21][C:20]2[CH:37]=[CH:38][C:39]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:40][C:19]=2[CH2:16][CH2:17][CH3:18])=[CH:27][CH:28]=1)[C:33]([O:35][CH3:36])=[O:34]

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 67184N-bromobutanimideHCID 2733832Lithium HexamethyldisilazideHCID 22459155HCID 22459155、化合物

生成物 1

HCID 15434957HCID 15434957、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of lithium bis(trimethylsilyl)amide (27.36 mL, 27.36 mmol) in dry THF ( 80 mL) was treated with trimethylsilyl chloride (5.94 mL, 46.76 mmol) at −78° C. To this mixture was added dropwise a solution of the product of Step B (10.80 g, 24.87 mmol) in THF (15 mL). The reaction mixture was stirred at −78° C. for 2 h. N-bromosuccinimide (4.65 g, 26.12 mmol) was added, and the mixture was allowed to warn to room temperature overnight. THF was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed once with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to provide methyl α-bromo-4-(3-(2-propyl-4-phenoxy-phenoxy)propoxy)phenylacetate as an oil.

後処理

  1. waitto warn to room temperature overnight
  2. customTHF was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed once with water
  5. dry with materialdried over sodium sulfate
  6. filtrationThe organic layer was filtered
  7. customevaporated

出典と根拠

ORDレコード
ord-205707eba6ed4554b6100294d5bbba36
出典データセット
uspto-grants-2002_06
特許番号
US06399640B1

反応ノート

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