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

HRID 1657653노트

반응식

HRID 1657653 반응식
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:3]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([CH:11]=1)[OH:10])[CH3:4].C[O:19][C:20]([CH:22]1[C:27](=O)[CH2:26][CH2:25][CH2:24][S:23]1)=O.Cl>C(O)C>[OH:10][C:9]1[C:8]2[C:27]3[CH2:26][CH2:25][CH2:24][S:23][C:22]=3[C:20](=[O:19])[O:12][C:7]=2[CH:6]=[C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])[CH:11]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 18379299Methyl 3-oxotetrahydrothiopyran-2-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 14.2 g. (0.06 mole) of 5-(3-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 magnesium silicate (60-100 mesh) and graded methanol/chloroform solvent mixtures. A total of 10 g. of crude solid was obtained frm the 1% methanol/chloroform fractions. The material was recrystallized twice from ethyl acetate/hexane to give 8.5 g. 40%) of colorless crystals, m.p. 131°-133°C. The proposed structure was confirmed by infrared and nuclear magnetic resonance spectra.

후처리

  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 frm the 1% methanol/chloroform fractions
  9. customThe material was recrystallized twice from ethyl acetate/hexane
  10. customto give 8.5 g

출처 및 근거

ORD 기록
ord-045ba0592bf84b2e87b80cc1ca5e0e4f
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03960871

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