Water → 2,2,2-Trichloroethyl 5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenylcarbamate

HRID 243798ノート

反応式

HRID 243798 の反応式
[NH2:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.C(N(CC)C(C)C)(C)C.Cl[C:26]([O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])=[O:27].O>C1COCC1>[C:8]([C:6]1[CH:5]=[C:4]([CH2:12][OH:13])[C:3]([O:14][CH3:15])=[C:2]([NH:1][C:26](=[O:27])[O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])[CH:7]=1)([CH3:11])([CH3:9])[CH3:10]

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 58366895(3-Amino-5-tert-butyl-2-methoxyphenyl)methanol

生成物 1

HCID 681068792,2,2-Trichloroethyl 5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenylcarbamate収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (3-amino-5-tert-butyl-2-methoxyphenyl)methanol (1.72 g, 8.23 mmol) and N,N-diisopropylethylamine (2.15 mL, 12.3 mmol) in THF (27.4 mL) was cooled to 0° C., and 2,2,2-trichloroethyl chloroformate (1.24 mL, 9.01 mmol) was added, followed by stirring the mixture for 10 minutes. Water was added to the reaction solution and the aqueous layer was extracted with ethyl acetate and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=75/25-50/50) to obtain 2.23 g of the captioned compound (71% yield).

後処理

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=75/25-50/50)

出典と根拠

ORDレコード
ord-1b36a8f1fb61491593b5af8626af9c2b
出典データセット
uspto-grants-2014_02
特許番号
US08653304B2

反応ノート

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