Triethylamine → HCID 21844643、化合物

HRID 1738624ノート

反応式

HRID 1738624 の反応式
[CH:1]([CH2:3][CH2:4][CH2:5][CH:6]1[O:11][CH:10]([OH:12])[CH2:9][CH2:8][CH2:7]1)=[O:2].CCN(CC)CC.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]([CH2:3][CH2:4][CH2:5][CH:6]1[O:11][CH:10]([O:12][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:9][CH2:8][CH2:7]1)=[O:2]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 21844652HCID 21844652、化合物

生成物 1

HCID 21844643HCID 21844643、化合物収率 90%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

In a 25 mL round bottomed flask was placed a solution of 6-(3-formylpropyl)-2-hydroxytetrahydropyran (153 mg, 0.89 mmol), DMAP (5 mg), and Et3N (0.4 mL) in CH2Cl2 (10 mL). The solution was cooled to 0° C., and tert-butyldimethylsilyl chloride (205 mg, 1.34 mmol) in CH2Cl2 (3 mL) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight, and then the solvent was removed under reduced pressure. Ether was added and the organic layer was washed with saturated NH4Cl twice followed by brine, dried over anhydrous magnesium sulfate, and then concentrated in vacuo. The residue was submitted to column chromatography on silica gel to afford 6-(3-formylpropyl)-2-(tert-butyldimethylsiloxy)tetrahydropyran as a clear yellow oil (206 mg, 90% yield): 1H NMR (CDCl3) δ 0.09 (s, 3H), 0.10 (s, 3H), 0.89 (s, 9H), 1.19-1.73 (m, 10H), 2.43 (m, 2H), 3.34 (t, 1H, J=5.7 Hz), 4.63 (d, 1H, J=9 Hz), 9.74 (s, 1H); 13C NMR (CDCl3) δ -4.0, 18.14, 18.41, 22.21, 25.81, 30.61, 33.83, 35.25, 43.70, 75.70, 97.26, 202.63. HRMS [CI (CH4)] calcd for C15H29O3Si: 285.1886 (M-H,)+. Found: 285.1890 (Δ-1.4 ppm).

後処理

  1. customIn a 25 mL round bottomed flask was placed
  2. temperatureto warm to room temperature overnight
  3. customthe solvent was removed under reduced pressure
  4. additionEther was added
  5. washthe organic layer was washed with saturated NH4Cl
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-243e160641584dbda79ae6354b51a544
出典データセット
uspto-grants-1999_10
特許番号
US05962744

反応ノート

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