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Methyl iodide → 9a-butyl-7-methoxymethoxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7862
ノート
印刷プレビュー

反応式

HRID 7862 の反応式
[CH2:1]([C:5]12[CH2:17][CH:16]([CH3:18])[C:15](=[O:19])[C:14]([CH3:20])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:21][CH2:22][O:23][CH3:24])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].[Li+].[CH3:26]C([N-]C(C)C)C.IC>C1COCC1>[CH2:1]([C:5]12[CH2:17][C:16]([CH3:26])([CH3:18])[C:15](=[O:19])[C:14]([CH3:20])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:21][CH2:22][O:23][CH3:24])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 67401243(2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 219908699a-butyl-7-methoxymethoxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

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 (2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (39 mg, 0.12 mmol) in anhydrous THF (1.0 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated with 0.4M LDA in THF (0.39 mL, 0.16 mmol). After stirring at 0° C. for 30 minutes, the yellow solution was cooled to −78° C. and treated with iodomethane (0.037 mL, 0.6 mmol). The resulting mixture was allowed to gradually warm to room temperature, then stirred at room temperature overnight. Workup as described in Example 18, step 2, afforded a crude product which was purified by PLC on a 0.1×20×20 cm silica gel GF plate, using 10:1 hexanes-EtOAc as developing solvent. The band at Rf 0.18-0.24 afforded 9a-butyl-7-methoxymethoxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (28 mg) as an oil.

後処理

  1. stirringAfter stirring at 0° C. for 30 minutes
  2. temperatureto gradually warm to room temperature
  3. stirringstirred at room temperature overnight
  4. customafforded a crude product which
  5. customwas purified by PLC on a 0.1×20×20 cm silica gel GF plate

出典と根拠

ORDレコード
ord-1cea5b97e21b47708df149edb4f91295
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07087599B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート