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

HRID 514144노트

반응식

HRID 514144 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:24][Si](C(C)(C)C)(C)C)[C:20]([O:22][CH3:23])=[O:21])[C:3]=1[CH3:32]>C(O)(C(F)(F)F)=O>[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]([OH:24])[C:20]([O:22][CH3:23])=[O:21])[C:3]=1[CH3:32]

참가 물질

3

반응물 1

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

생성물 1

HCID 67126228Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate수율 70.3%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매2회

반응 조건

온도
60 °C

실험 절차

Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetate (537.8 mg, 1.01 mmol) was dissolved in 4.0 mL TFA and heated to 60° C. The reaction was monitored by HPLC and turned dark quickly after addition of TFA. The reaction was completed after 1 h by HPLC, was removed from heat and diluted with toluene (20 mL) and concentrated in vacuo. This dilution/concentration was repeated twice more and the color was observed to diminished on each cycle. Purification via column chromatography using silica gel with EtOAc and heptane gave rise to desired product (297.9 mg, 0.71 mmol). 1H-NMR: (400 MHz, CDCl3): δ 10.34 (s, broad, 1H); 8.40 (d, J=8.0 Hz, 1H); 7.60-7.56 (m, 1H); 7.52-7.46 (m, 2H); 7.38-7.35 (m, 1H); 7.32-7.28 (m, 2H); 5.26 (s, 1H); 3.74 (s, 3H); 2.62 (s, 3H).

후처리

  1. customwas removed
  2. temperaturefrom heat
  3. additiondiluted with toluene (20 mL)
  4. concentrationconcentrated in vacuo
  5. concentrationThis dilution/concentration
  6. customPurification via column chromatography

출처 및 근거

ORD 기록
ord-86fcb47f27a544e1967724903dc40495
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102614B2

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