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Sodium hydride → HCID 18704224, 화합물

HRID 2288296
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HRID 2288296 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 10978586Silane, (4-iodobutoxy)trimethyl-HCID 18704219HCID 18704219, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 18704224HCID 18704224, 화합물수율 76.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6118d6b7654447e183a59545e74e62c1
출처 데이터셋
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06087509

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