Dimethylformamide → HCID 25140998, 화합물

HRID 1511414

반응식

HRID 1511414 반응식
[CH:1](N(CC)C(C)C)(C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([OH:18])[CH:17]=1.[CH3:20][O:21][CH2:22]Cl.CN(C)[CH:26]=[O:27]>>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH2:20][O:21][CH3:22])[CH:15]=[C:14]([O:19][CH2:1][O:27][CH3:26])[CH:13]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 71648FlamenolHCID 81531Diisopropylethylamine

생성물 1

HCID 25140998HCID 25140998, 화합물수율 43%

반응 조건

온도
0 °C

실험 절차

N,N-diisopropylethylamine (3.15 mL, 18.1 mmol) was added to 5-methoxybenzene-1,3-diol (634 mg, 4.52 mmol) in anhydrous N,N-dimethylformamide (12.6 mL) over five minutes at room temperature. After 30 minutes, the solution was cooled to 0° C., methoxy methylchloride (3.02 mL, 18.1 mmol) was added, and the solution was warmed to room temperature over 12 hours. The reaction was quenched by the addition of saturated aqueous NaHCO3 at 0° C. and extracted with EtOAc (3×10 mL). Combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 6:1→4:1 Hexane:EtOAc) to afford 8 as a yellow amorphous solid (441 mg, 43%): 1H NMR (CDCl3, 500 MHz) 6.29 (t, J=2.2 Hz, 1H), 6.21 (d, J=2.2 Hz, 2H), 5.07 (s, 4H), 3.69 (s, 3H), 3.40 (s, 6H); 13C NMR (CDCl3, 125 MHz) 161.394, 159.0 (2C), 97.2, 96.2 (2C), 94.5 (2C), 56.1, 55.4 (2C); IR (film) νmax 2997, 2955, 2903, 2827, 1601, 1475, 1400, 1215, 1194, 1146, 1032, 991, 924, 829, 685 cm−1; HRMS (ESI+) m/z: [M+Na]+ calcd for C11H16O5, 251.0895; found, 251.0910.

후처리

  1. temperaturethe solution was warmed to room temperature over 12 hours
  2. customThe reaction was quenched by the addition of saturated aqueous NaHCO3 at 0° C.
  3. extractionextracted with EtOAc (3×10 mL)
  4. washCombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography (SiO2, 6:1→4:1 Hexane:EtOAc)

출처 및 근거

ORD 기록
ord-0b6598458edc451aa2dbc163269f6d9f
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212012B2

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