Diethyl Ether → HCID 131726817, 화합물

HRID 1624262노트

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HRID 1624262 반응식
[C@@H:1]1(CO)[CH2:3][C@H:2]1[CH2:4][OH:5].[H-].[Na+].[C:10]([Si:14](C)(C)Cl)([CH3:13])([CH3:12])[CH3:11].C([O:20][CH2:21][CH3:22])C.[CH2:23]1COCC1>>[OH:5][CH2:4][C@@H:2]1[CH2:3][C@H:1]1[C:21]([CH3:22])([CH3:23])[O:20][SiH2:14][C:10]([CH3:13])([CH3:12])[CH3:11]

참가 물질

6

반응물 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 111159962345-75-7

생성물 1

HCID 131726817HCID 131726817, 화합물수율 65%

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온도
0 °C

실험 절차

To a cooled (0° C.) stirred solution of trans-1,2-cyclopropanedimethanol (2.0 g, 20 mmol) in THF (40 mL) was slowly added NaH (60% dispersion in oil, 0.80 g, 20 mmol). Stirring was continued at 0° C. for 10 min. tert-Butyldimethylchlorosilane (3.0 g, 20 mmol) was added. The thick white slurry was allowed to warm to room temperature and stirring was continued for 10 min. The resultant mixture was poured into diethyl ether (400 mL) and washed with 10% K2CO3 (100 mL) then washed again with brine (100 mL). The separated organic layer was dried over Na2SO4 and concentrated. The crude material was purified by flash column chromatography (5 cm id., 100 g silica gel, eluted with 5:1 hexanes/ethyl acetate) to give the mono-protected desired product as a clear oil (2.8 g, 65%). 1H NMR (CDCl3) δ 0.05 (s, 6H), 0.41-0.53 (m, 2H), 0.89 (s, 9H), 0.89-1.04 (m, 2H), 1.41 (t, 1H, J=5.8 Hz), 3.41-3.50 (m, 3H), 3.60 (dd, 1H, J=11.2, 5.8 Hz).

후처리

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitwas continued for 10 min
  4. washwashed with 10% K2CO3 (100 mL)
  5. washthen washed again with brine (100 mL)
  6. dry with materialThe separated organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude material was purified by flash column chromatography (5 cm id., 100 g silica gel, eluted with 5:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-bb3c67e5e92140db8eae48bff8049252
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778967B2

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