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Chloroform → {[tert-Butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetaldehyde

HRID 1171772
ノート
印刷プレビュー

反応式

HRID 1171772 の反応式
[Si:1]([O:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10](OC)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Si:1]([O:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]
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 6212ChloroformHCID 14487Diisobutylaluminum hydrideHCID 86623126Methyl {[tert-butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetate

生成物 1

HCID 86623127{[tert-Butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetaldehyde収率 99.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

Methyl {[tert-butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetate (0.5 g, 1.61 mmol) was dissolved in toluene (10 mL) and cooled to −78° C. under a nitrogen atmosphere. DIBAL (1.0M in toluene, 1.9 mL, 1.93 mmol) was added slowly and the mixture was stirred at −78° C. for 1 h. The reaction mixture was poured onto a mixture of ice (20 g) and CHCl3 (20 mL). The mixture was stirred at r.t. for 30 minutes. The layers were separated and the water phase extracted with CHCl3. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated, obtaining 99% (0.45 g) of the title compound. The product was used directly in the next step without further purification.

後処理

  1. stirringThe mixture was stirred at r.t. for 30 minutes
  2. customThe layers were separated
  3. extractionthe water phase extracted with CHCl3
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-8e50959f9d4047c59a60dde50e94b9d0
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07829707B2

反応ノート

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