Imidazole → HCID 178472500、化合物

HRID 271345ノート

反応式

HRID 271345 の反応式
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].CN(C=O)C>O>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

6

反応物 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178472486HCID 178472486、化合物

生成物 1

HCID 178472500HCID 178472500、化合物収率 90.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 3 g of cis-4-hydroxy-cyclohexanecarboxylic acid ethyl ester, 3 g of imidazole, 33 g of tert-butyldimethylsilyl-chloride, and 6 mL of DMF was stirred under inert atmosphere overnight. The mixture was diluted with 250 mL of water and extracted into 3×50 mL portions of ether. The combined ether extracts were washed with 2×50 mL of water, dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum overnight gave 4.5 g of product as a colorless oil: 1H NMR (400 MHz, CDCl3) 4.1 (dd, 2H), 3.58 (m, cis isomer, 0.85H), 2.2 (m, 1H), 1.95 (m, 4H), 1.6 (m, 1H), 1.5 (m, 1H), 1.22 (m, 6H), 0.9 (s, 9H), 0.04 (s, 6H).

後処理

  1. extractionextracted into 3×50 mL portions of ether
  2. washThe combined ether extracts were washed with 2×50 mL of water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customDrying under vacuum overnight

出典と根拠

ORDレコード
ord-e6fdad159d8548b28af033b002538279
出典データセット
uspto-grants-2008_11
特許番号
US07452893B2

反応ノート

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