Benzene → Methyl 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-ethenyl]benzoate

HRID 129250ノート

反応式

HRID 129250 の反応式
[CH3:1][Si](C)(C)[N-][Si](C)(C)C.[K+].[C:11]1(C)C=CC=C[CH:12]=1.[CH3:18][C:19]1([CH3:43])[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[C:25]2[CH:24]=[C:23](C(C3C=CC(C(OC)=O)=CC=3)=O)[CH:22]=[CH:21][C:20]1=2.[C:44]([O-:47])(O)=[O:45].[Na+].[CH:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCCl.CCCCCC>[CH3:18][C:19]1([CH3:43])[CH2:28][CH2:27][C:26]([CH3:29])([CH3:30])[C:25]2[CH:24]=[C:23]([C:11]([C:49]3[CH:54]=[CH:53][C:52]([C:44]([O:47][CH3:1])=[O:45])=[CH:51][CH:50]=3)=[CH2:12])[CH:22]=[CH:21][C:20]1=2

参加物

8

反応物 5

HCID 241Benzene2 回HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 10784070Methyl 4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoate

生成物 1

HCID 9997911Methyl 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-ethenyl]benzoate収率 80%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 21226440Methylenechloride Hexane溶媒

実験手順

To a suspension of methyltriphenylphosphonium bromide (0.78 g, 2.18 mmol) in 5 mL of benzene under argon at room temperature was added a 0.5M solution of potassium hexamethyldisilazide in toluene (4.4 mL, 2.2 mmol), and the yellow solution was stirred for 5 min. A solution of keto-ester 3 (0.51 g, 1.455 mmol) in 7 mL of benzene was added, and the orange solution was stirred for 1 h at room temperature. The reaction mixture was poured into saturated aqueous NaHCO3 and extracted with 40% ethyl acetate/hexane. The combined organic layers were dried over anhydrous MgSO4, filtered through a plug of silica gel, and concentrated to afford a solid. Flash chromatography (30% dichloromethane/hexane) yielded the desired product 16 as a white solid (0.405 g, 80%): m.p. 117°-118° C.; Rf 0.2 (25% CH2Cl2 /hexane). The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy.

後処理

  1. stirringthe orange solution was stirred for 1 h at room temperature
  2. extractionextracted with 40% ethyl acetate/hexane
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. filtrationfiltered through a plug of silica gel
  5. concentrationconcentrated
  6. customto afford a solid

出典と根拠

ORDレコード
ord-71076597244a4d728395553e1843a512
出典データセット
uspto-grants-1995_11
特許番号
US05466861

反応ノート

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