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Sodium hydride → HCID 18704224、化合物

HRID 2288296
ノート
印刷プレビュー

反応式

HRID 2288296 の反応式
[H-].[Na+].[O:3]=[C:4]1[N:8]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)[C:7](=[O:21])[C:6]2([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[NH:5]1.[H][H].C[Si](C)(C)[O:31][CH2:32][CH2:33][CH2:34][CH2:35]I>CN(C)C=O>[O:3]=[C:4]1[N:8]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:18])[F:19])[CH:10]=2)[C:7](=[O:21])[C:6]2([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[N:5]1[CH2:35][CH2:34][CH2:33][CH2:32][OH:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 10978586Silane, (4-iodobutoxy)trimethyl-HCID 18704219HCID 18704219、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 18704224HCID 18704224、化合物収率 76.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

28 mg of 50% sodium hydride and 3 ml of dimethylformamide are introduced, agitation is carried out at ambient temperature for 5 minutes, 170 mg of the product obtained in Stage 3 above is added and the whole is left under agitation for 20 minutes until the release of hydrogen has stopped. 202 mg of O-trimethylsilyl-4-iodo-n-butanol is then added and the reaction medium is left under agitation for 2 hours. After hydrolysis using saturated ammonium chloride, extraction is carried out with ethyl acetate. The organic phases are combined, washed with water, dried, filtered and concentrated. The residue is solubilized in 10 ml of methanol and 0.5 ml of 2N hydrochloric acid is added. After agitation for 5 minutes, the solution is neutralized by the addition of saturated sodium hydrogen carbonate and extraction is carried out with ethyl acetate. The organic phases are combined, dried, filtered and concentrated. After chromatography on silica eluting with methylene chloride-acetone: 9-1, 158 mg of expected product (white solid) is obtained. M.p.=145° C.

後処理

  1. waitthe reaction medium is left under agitation for 2 hours
  2. customAfter hydrolysis
  3. extractionammonium chloride, extraction
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. addition0.5 ml of 2N hydrochloric acid is added
  9. waitAfter agitation for 5 minutes
  10. additionthe solution is neutralized by the addition of saturated sodium hydrogen carbonate and extraction
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-6118d6b7654447e183a59545e74e62c1
出典データセット
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06087509

反応ノート

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