Diethyl Ether → HCID 131726817、化合物

HRID 1624262ノート

反応式

HRID 1624262 の反応式
[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]

参加物

6

反応物 5

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

生成物 1

HCID 131726817HCID 131726817、化合物収率 65%

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bb3c67e5e92140db8eae48bff8049252
出典データセット
uspto-grants-2014_07
特許番号
US08778967B2

反応ノート

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