Imidazole → Tert-butyl(dimethyl)({(1s,2r,4s,6s)-1-methyl-4-[(triethylsilyl)oxy]-7-oxabicyclo[4.1.0]hept-2-yl}oxy)silane

HRID 388745

反応式

HRID 388745 の反応式
[Si:1]([O:8][C@H:9]1[C@:15]2([CH3:16])[C@@H:13]([O:14]2)[CH2:12][C@H:11]([OH:17])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.Cl[Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26].O>CN(C)C=O>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][C@@H:9]1[CH2:10][C@@H:11]([O:17][Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])[CH2:12][C@H:13]2[C@:15]1([CH3:16])[O:14]2)([CH3:7])([CH3:6])[CH3:5]

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 13819ChlorotriethylsilaneHCID 87628830(1s,3s,5r,6s)-5-{[Tert-butyl(dimethyl)silyl]oxy}-6-methyl-7-oxabicyclo[4.1.0]heptan-3-ol

生成物 1

HCID 87538262Tert-butyl(dimethyl)({(1s,2r,4s,6s)-1-methyl-4-[(triethylsilyl)oxy]-7-oxabicyclo[4.1.0]hept-2-yl}oxy)silane収率 99%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The compound of Example 16D (4.71 g, 18.2 mmol) and imidazole (1.76 g, 25.6 mmol, 1.4 equivalents) were dissolved in 36 mL of dimethylformamide. Then chlorotriethylsilane (3.34 g, 21.9 mmol) was added, and the reaction was stirred at ambient temperature for 2 hours. 125 mL of Water was added to the reaction mixture. Two layers of liquors were obtained and about 6 g of upper layer was separated. Then the lower aqueous layer was extracted three times with 100 mL each of tert-butyl methyl ether. The combined organic layers were washed with 125 mL of 10% aqueous NaCl, dried over MgSO4, filtered and concentrated in vacuo to afford the titled compound (6.71 g, 99%).

後処理

  1. customTwo layers of liquors were obtained
  2. customabout 6 g of upper layer was separated
  3. extractionThen the lower aqueous layer was extracted three times with 100 mL each of tert-butyl methyl ether
  4. washThe combined organic layers were washed with 125 mL of 10% aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f92a8ae7e6494eedb1f8edc7e8fae54c
出典データセット
uspto-grants-2013_02
特許番号
US08377913B2

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