Methoxymethyl-triphenylphosphonium chloride → 2,6-Diisopropyl-4-bromo-3-methoxystyrene

HRID 338211ノート

反応式

HRID 338211 の反応式
[Cl-].[CH3:2][O:3]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:24][Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH:34]([C:37]1[CH:44]=[C:43]([Br:45])[CH:42]=[C:41]([CH:46]([CH3:48])[CH3:47])[C:38]=1[CH:39]=O)([CH3:36])[CH3:35]>C1COCC1>[CH:34]([C:37]1[C:44]([O:3][CH3:2])=[C:43]([Br:45])[CH:42]=[C:41]([CH:46]([CH3:48])[CH3:47])[C:38]=1[CH:39]=[CH2:24])([CH3:36])[CH3:35]

参加物

5

反応物 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2733832Lithium HexamethyldisilazideHCID 574376682,6-Diisopropyl-4-bromobenzaldehyde

生成物 1

HCID 867326662,6-Diisopropyl-4-bromo-3-methoxystyrene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Methoxymethyl triphenylphosphonium chloride (18.68 g, 54.5 mmol) was suspended in 200 mL of THF at −78° C. Lithium hexamethyldisilazide (1.0 M in THF, 50 mL) was added dropwise. The resulting mixture was warmed up to 0° C. with stirring. After cooling the solution to −78° C., 2,6-diisopropyl-4-bromobenzaldehyde (11.5 g, 42.7 mmol) in 20 mL of THF was added dropwise. The mixture was slowly warmed up to room temperature and continually stirred overnight. After regular work up, the crude product was distilled at 165° C. under vacuum to afford 2,6-diisopropyl-4-bromo-3-methoxystyrene (10 g). This product was dissolved in 20 mL of dioxane and 100 mL of 18% HCl solution and refluxed at 100° C. for 6 h. After regular work up, the crude product was distilled at 160° C. under vacuum to afford 2,6-diisopropyl-4-bromophenylacetaldehyde (7.5 g).

後処理

  1. temperatureAfter cooling the solution to −78° C.
  2. temperatureThe mixture was slowly warmed up to room temperature and continually stirred overnight
  3. distillationAfter regular work up, the crude product was distilled at 165° C. under vacuum

出典と根拠

ORDレコード
ord-8321b48642ee46c3a50c0dbff36336a8
出典データセット
uspto-grants-2014_11
特許番号
US08889864B2

反応ノート

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