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

HRID 514143
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HRID 514143 반응식
[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]
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매

1
HCID 21226129Dichloromethane methanol용매

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온도
23 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0d0c0001155f4542844294a693736bed
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102614B2

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