Hydrochloric Acid → 1,2-Dihydro-10-hydroxy-8-(3-methyl-2-octyl)-5-oxo-3H,5H-thiopyrano[2,3-c][1]benzopyran

HRID 1579103ノート

反応式

HRID 1579103 の反応式
C[CH2:2][CH:3]([C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[C:14]([CH:16]=1)[OH:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O=[C:19]1[CH2:24][CH2:23][CH2:22][S:21][CH:20]1[C:25](OC)=[O:26].Cl.[CH2:30](O)C>>[OH:17][C:12]1[C:13]2[C:19]3[CH2:24][CH2:23][CH2:22][S:21][C:20]=3[C:25](=[O:26])[O:15][C:14]=2[CH:16]=[C:10]([CH:3]([CH:4]([CH3:30])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH3:2])[CH:11]=1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 18379299Methyl 3-oxotetrahydrothiopyran-2-carboxylateHCID 215326095-(Methyl-2-octyl)resorcinol

生成物 1

HCID 214339161,2-Dihydro-10-hydroxy-8-(3-methyl-2-octyl)-5-oxo-3H,5H-thiopyrano[2,3-c][1]benzopyran

実験手順

A solution of 14.2 g. (0.06 mole) of 5-(methyl-2-octyl)resorcinol and 11.1 g. (0.063 mole) of methyl 3-oxo-2,3,4,5-tetrahydro-6H-thiopyran-2-carboxylate in 90 ml. of absolute ethanol was cooled in an ice-salt bath and saturated with anhydrous hydrogen chloride. After standing for 2 days at room temperature, the ethanol was removed on a rotary evaporator. The residue was dissolved in ether, washed with sodium bicarbonate solution and dried over sodium sulfate. Evaporation of the solvent gave 28.0 g. of residue which was chromatographed using Florisil (60-100 mesh) and graded methanol/chloroform solvent mixtures. A total of 10 g. of crude solid was obtained from the 1% methanol/chloroform fractions. The material was recrystallized twice from ethyl acetate/hexane to give 8.5 g. (40%) colorless crystals, m.p. 131°-133°C. The proposed structure was confirmed by IR and NMR spectra.

後処理

  1. customthe ethanol was removed on a rotary evaporator
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent
  6. customgave 28.0 g
  7. customof residue which was chromatographed
  8. customof crude solid was obtained from the 1% methanol/chloroform fractions
  9. customThe material was recrystallized twice from ethyl acetate/hexane
  10. customto give 8.5 g

出典と根拠

ORDレコード
ord-e6d5b0d27d6e45e1b1948a0f3e0b4bef
出典データセット
uspto-grants-1976_02
特許番号
US03940421

反応ノート

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