Dimethylformamide → HCID 25140998、化合物

HRID 1511414ノート

反応式

HRID 1511414 の反応式
[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

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 71648FlamenolHCID 81531Diisopropylethylamine

生成物 1

HCID 25140998HCID 25140998、化合物収率 43%

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0b6598458edc451aa2dbc163269f6d9f
出典データセット
uspto-grants-2012_07
特許番号
US08212012B2

反応ノート

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