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

반응식

HRID 388745 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f92a8ae7e6494eedb1f8edc7e8fae54c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377913B2

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