Tetrahydrofuran → (1S,4aS,7aR)-1-[1-(ethoxy)ethoxy]-7-[2-(hydroxy)ethyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester

HRID 377085노트

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HRID 377085 반응식
[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17]([CH:20]=O)[C@@H:7]2[C@H:8]([O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[O:9][CH:10]=1)=[O:4].CI.[Mg].[Cl-].[NH4+].[O:27]1CCC[CH2:28]1>>[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17]([CH2:20][CH2:28][OH:27])[C@@H:7]2[C@H:8]([O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[O:9][CH:10]=1)=[O:4]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 57167711HCID 57167711, 화합물HCID 86584867HCID 86584867, 화합물

생성물 1

HCID 57042520(1S,4aS,7aR)-1-[1-(ethoxy)ethoxy]-7-[2-(hydroxy)ethyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester수율 77%

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온도
-78 °C

실험 절차

An anhydrous tetrahydrofuran solution containing 100 mg of (1S,4aS,7aR)-1-[1-(ethoxy)ethoxy]-7-formyl-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester was cooled to -78° C. under argon gas atmosphere followed by dropping 0.38 ml of magnesium methyliodide (0.98 M tetrahydrofuran solution). Two hours later, saturated aqueous ammonium chloride solution was added to the reaction mixture followed by extraction with ethyl acetate. After washing the organic phase with brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a pale yellow oil from the hexane-ether eluate in the form of (1S,4aS,7aR)-1-[1-(ethoxy)ethoxy]-7-[2-(hydroxy)ethyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester (81 mg, yield: 77%). the physicochemical properties of this compound are described below. 1H-NMR (δ ppm, in CDCl3): 1.03-1.39 (9H,m), 1.68-3.24 (5H,m), 3.72 (3H,s), 3.40-3.88 (2H,m), 4.72-5.08 (2H,m), 5.52 (1H,br,s), 7.47-7.49 (1H,m)

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washAfter washing the organic phase with brine, it
  3. dry with materialwas dried over magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-03eea8d0b25a47b4b1da65268ca0af42
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022888

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