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Trimethylsilyldiazomethane → Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetate

HRID 514143
ノート
印刷プレビュー

反応式

HRID 514143 の反応式
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[C:20]([OH:22])=[O:21])[C:3]=1[CH3:31].[Si](C=[N+]=[N-])(C)(C)[CH3:33].BrC1C2C(=CC=CC=2)C(C2C=CC(Cl)=CC=2)=C(C(O[Si](C(C)(C)C)(C)C)C=O)C=1C>C(Cl)Cl.CO>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:4]([CH:19]([O:23][Si:24]([C:27]([CH3:28])([CH3:30])[CH3:29])([CH3:25])[CH3:26])[C:20]([O:22][CH3:33])=[O:21])[C:3]=1[CH3:31]
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 167693TrimethylsilyldiazomethaneHCID 671261952-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetic acidHCID 866915662-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetaldehyde

生成物 1

HCID 67126260Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetate収率 78%

試薬・触媒・溶媒

1
HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
23 °C

実験手順

Crude 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetic acid 0.740 g, 1.4 mmol)was dissolved in 20 mL DCM-MeOH (50-50, v/v) and combined with TMS-diazomethane solution (7.0 mL, 2.0 M in hexanes) and allowed to stir 6 hrs at 23° C. The reaction was cooled on ice and quenched by the slow addition of TFA (500 μL) which simultaneously removed the yellow color from the reaction mixture. Mixture was diluted with DCM and washed with brine, then dried and concentrated in vacuo. Purification by silica gel chromatography with EtOAc in hexanes provided purified material (537.8 mg, 78% yield) from the 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetaldehyde. 1H-NMR: (400 MHz, MeOH-d4): δ 8.39 (d, J=8.0 Hz, 1H); 7.58-7.54 (m, 1H); 7.50-7.47 (m, 2H); 7.37-7.33 (m, 2H); 7.27-7.21 (m, 2H); 5.31 (s, 1H); 3.69 (s, 3H); 2.67 (s, 3H); 0.83 (s, 9H); −0.04 (s, 3H); −0.27 (s, 3H).

後処理

  1. temperatureThe reaction was cooled on ice
  2. customquenched by the slow addition of TFA (500 μL) which
  3. customsimultaneously removed the yellow color from the reaction mixture
  4. additionMixture was diluted with DCM
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography with EtOAc in hexanes
  9. customprovided

出典と根拠

ORDレコード
ord-0d0c0001155f4542844294a693736bed
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102614B2

反応ノート

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