Diethyl Ether → 3-[4-(3-Hydroxy-2,2-dimethoxypropoxymethyl)benzylidene]-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one

HRID 251521노트

반응식

HRID 251521 반응식
Br[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[C:8]2[C:13]3([CH3:17])[C:14]([CH3:16])([CH3:15])[CH:10]([CH2:11][CH2:12]3)[C:9]2=[O:18])=[CH:5][CH:4]=1.[CH3:21][O:22][C:23]([O:28][CH3:29])([CH2:26][OH:27])[CH2:24][OH:25].CC([O-])(C)C.[K+].C(OCC)C>C1COCC1.CC(O)(C)C.O>[OH:25][CH2:24][C:23]([O:28][CH3:29])([O:22][CH3:21])[CH2:26][O:27][CH2:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[C:8]2[C:13]3([CH3:17])[C:14]([CH3:16])([CH3:15])[CH:10]([CH2:11][CH2:12]3)[C:9]2=[O:18])=[CH:5][CH:4]=1

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 111263102,2-Dimethoxypropane-1,3-diolHCID 23665647Potassium tert-butoxideHCID 672920233-(4-Bromomethylbenzylidene)-4,7,7-trimethylbicyclo[2.2.1]-heptan-2-one

생성물 1

HCID 672911983-[4-(3-Hydroxy-2,2-dimethoxypropoxymethyl)benzylidene]-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one

시약·촉매·용매 3

HCID 962Water용매HCID 6386tert-Butanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

A solution of 3-(4-bromomethylbenzylidene)-4,7,7-trimethylbicyclo[2.2.1]-heptan-2-one (C. Bouillon, C. Vayssie, in Ger. Offen., (Oreal S. A., Fr.). Appl: DE 19780314. 78-2811041, 1978, p. 71. C. Bouillon, C. Vayssie, in Fr. Demande, (Oreal S. A., Fr.), Fr, Number 2421878, 1979, p. 31. C. Bouillon, C. Vayssie, (Oreal S. A., Fr.). Ca, Number 1113480, 1981, p. 61) (10.0 g, 30 mmol) in THF (30 ml) is slowly added dropwise at 40° C. with stirring to a solution of 2,2-dimethoxy-1,3-propanediol (M. W. Chun, D. H. Shin, H. R. Moon, J. Lee, H. Park, L. S. Jeong, Bioorg. Med. Chem. Lett 1997, 7, 1475. E. Cesarotti, P. Antognazza, M. Pallavicini, L. Villa, Helv. Chim. Acta 1993, 76, 2344. E. L. Ferroni, V. DiTella, N. Ghanayem, R. Jeske, C. Jodlowski, et al., J. Org. Chem. 1999, 64, 4943) (8.17 g, 60 mmol) and t-BuOK (4.50 g, 40 mmol) in t-BuOH (150 ml). E is stirred at 40° C. for 30 min and subsequently at the reflux temperature for 1 h. After the reaction mixture has been cooled, diethyl ether (30 ml) and water (100 ml) are added. The organic phase is separated off, and the aqueous phase is extracted with diethyl ether (3×50 ml). The combined organic phases are washed with saturated sodium chloride solution (3×70 ml) and dried over magnesium sulfate; the solvent is removed. Work-up by column chromatography using ethyl acetate:cyclohexane 1:1 gives

후처리

  1. temperatureAfter the reaction mixture has been cooled
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with diethyl ether (3×50 ml)
  4. washThe combined organic phases are washed with saturated sodium chloride solution (3×70 ml)
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent is removed
  7. customgives

출처 및 근거

ORD 기록
ord-123912082d0a4e4ca6f8eb6422a392a2
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863478B2

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