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9-(t-Butyldimethylsilyloxy)-1-nonyne → 4-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1859292
ノート
印刷プレビュー

反応式

HRID 1859292 の反応式
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:48]=[CH:47][C:30]2[C:31](=[O:46])[C:32]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=3)([CH3:35])[CH2:33][O:34][C:29]=2[CH:28]=1>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:31]1([OH:46])[C:30]2[CH:47]=[CH:48][C:27]([O:26][CH2:25][O:24][CH3:23])=[CH:28][C:29]=2[O:34][CH2:33][C:32]1([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:40][CH:41]=1)[CH3:35])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]
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 140273559-(t-Butyldimethylsilyloxy)-1-nonyneHCID 154817637-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-oneHCID 178418339Butyllithium

生成物 1

HCID 220330974-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman収率 100%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
-78 °C

実験手順

9-(t-Butyldimethylsilyloxy)-non-1-yne (0.46 g, 1.8 mmol) was dissolved in dry tetrahydrofuran (8 ml) under argon atmosphere and then cooled to -78° C. 2.5M n-Butyllithium (n-BuLi) (0.7 ml, 1.68 mmol) was slowly added dropwise thereto and then the mixture was stirred for 30 minutes. To the mixture was added dropwise 7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran-4-one (200 mg, 6.6 mmol) dissolved in dry tetrahydrofuran (4 ml), and then the reaction mixture was slowly warmed to room temperature. The reaction solution was quenched with water and then extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to obtain 350 mg (yield: >100%) of the title compound as a colorless oil.

後処理

  1. temperaturethe reaction mixture was slowly warmed to room temperature
  2. customThe reaction solution was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-90f9d9fb21d34202b0f54bb52b27175b
出典データセット
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06153768

反応ノート

読み込み中…

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