Hydrochloric Acid → {5-[3-(Trifluoromethyl)phenyl]furan-2-yl}methanol

HRID 1112740

反応式

HRID 1112740 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.[CH2:21]=[O:22].Cl>O1CCCC1>[OH:22][CH2:21][C:11]1[O:10][C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14208689HCID 14208689、化合物HCID 178418339Butyllithium

生成物 1

HCID 7782745{5-[3-(Trifluoromethyl)phenyl]furan-2-yl}methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

2-(3-Trifluoromethylphenyl)-furan (J. Chem. Soc. (C) 1968, 2737 and Acta Chem Scand. 24, 2379 (1970))(21.2 g; 0.1 mole) was stirred in tetrahydrofuran (100 ml), cooled to -40° C. and n-butyl lithium (0.1 mole, solution in hexane) was added dropwise. After stirring for 1 hour at -40° C., paraformaldehyde (3.3 g; 0.11 mole) was added gradually. The mixture was stirred at -40° C. for 30 minutes, then the temperature was allowed to rise. At 10° C. an exothermic reaction set in and the temperature gradually rose to 40° C. (over 10 minutes), then gradually fell back to 20° C. After stirring for further 1 hour the clear brown solution was poured onto ice/water, adjusted to pH ca 4 with dilute hydrochloric acid and extracted via ethyl acetate. The dried acetate extract (MgSO4) was evaporated to give a brownish yellow viscous oil which was distilled in vacuo to give 2-hydroxymethyl-5-(3-trifluoromethylphenyl)-furan as a colourless liquid b.p. 125° C./0.5 mm., (16.2 g), which on standing gave crystals, m.p. 45° C.

後処理

  1. stirringThe mixture was stirred at -40° C. for 30 minutes
  2. customAt 10° C. an exothermic reaction
  3. customgradually rose to 40° C.
  4. custom(over 10 minutes)
  5. customgradually fell back to 20° C
  6. stirringAfter stirring for further 1 hour the clear brown solution
  7. additionwas poured onto ice/water
  8. extractionextracted via ethyl acetate
  9. extractionThe dried acetate extract (MgSO4)
  10. customwas evaporated
  11. customto give a brownish yellow viscous oil which
  12. distillationwas distilled in vacuo

出典と根拠

ORDレコード
ord-dc94b9fab5b449838cdeabbfa96f6b64
出典データセット
uspto-grants-1978_10
特許番号
US04123529

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