Diethyl Ether → 2,2-Dimethyl-4-(1-naphthyl)-7-chromanol

HRID 838903

반응식

HRID 838903 반응식
[CH3:1][Li].[OH:3][C:4]1C=C2[C:7]([CH:8]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[CH2:9]C(=O)O2)=[CH:6][CH:5]=1.[CH3:25][CH2:26][O:27][CH2:28][CH3:29]>C(O)(=O)C>[CH3:25][C:26]1([CH3:1])[CH2:9][CH:8]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:7]2[C:28](=[CH:29][C:4]([OH:3])=[CH:5][CH:6]=2)[O:27]1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 205705223,4-Dihydro-7-hydroxy-4-(1-naphthyl)coumarinHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 205705012,2-Dimethyl-4-(1-naphthyl)-7-chromanol

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a stirred solution of methyl-lithium in ether (120 ml., 1.9M solution) at room temperature was added over 0.5 hours finely powdered 3,4-dihydro-7-hydroxy-4-(1-naphthyl) coumarin (14.5g, 0.05 moles). After refluxing for 1 hour a purple solid precipitated out of solution and the reaction mixture was allowed to cool, acidified with dilute hydrochloric acid and extracted with ether (3×). The combined ether extracts were dried and removal of solvent gave a dark coloured oil which was refluxed overnight in glacial acetic acid. The glacial acetic acid was removed in vacuo and the residue dissolved in ether, washed with water, saturated sodium bicarbonate solution and dried. Removal of solvent gave an extremely viscous oil, column chromatography of which on silica, eluting with 40°-60° petrol: ether (gradually increasing concentration of ether) gave the required chroman as a low melting pale yellow solid (9.4g., 76%).

후처리

  1. temperatureAfter refluxing for 1 hour a purple solid
  2. customprecipitated out of solution
  3. temperatureto cool
  4. extractionextracted with ether (3×)
  5. dry with materialThe combined ether extracts were dried
  6. customremoval of solvent
  7. customgave a dark coloured oil which
  8. customThe glacial acetic acid was removed in vacuo
  9. dissolutionthe residue dissolved in ether
  10. washwashed with water, saturated sodium bicarbonate solution
  11. customdried
  12. customRemoval of solvent
  13. customgave an extremely viscous oil, column chromatography of which on silica
  14. washeluting with 40°-60° petrol
  15. temperatureether (gradually increasing concentration of ether)

출처 및 근거

ORD 기록
ord-b3a56ba6466c4f26ae06ef5ec7841103
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04093631

연결된 노트

불러오는 중…