Hydrochloric Acid → ethyl (3-{3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]propyl}phenoxy)-acetate

HRID 2389380노트

반응식

HRID 2389380 반응식
[H-].[Li+].[C:3]1([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=1)[O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].Cl>CN(C=O)C>[C:3]1([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][C:13](=[O:16])[N:14]([CH2:24][CH2:25][CH2:26][C:27]3[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=3)[O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:15]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 62714Lithium hydrideHCID 227488105-(Diphenylmethyl)-2-pyridoneHCID 86637892Ethyl [3-(3-iodopropyl)phenoxy]acetate

생성물 1

HCID 59145362ethyl (3-{3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]propyl}phenoxy)-acetate수율 74.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a mixture of LiH (6.20 g) in DMF (100 mL) was added a solution of 5-(diphenylmethyl)-2(1H)-pyridinone (82.4 g) in DMF (500 mL) at ambient temperature. A solution of ethyl [3-(3-iodopropyl)phenoxy]acetate (118 g) in DMF (300 mL) was added dropwise to the mixture at ambient temperature over 30 minutes and the mixture was stirred at the same temperature for 24 hours. The resulting mixture was poured into 1M HCl aqueous solution (800 mL) at 0° C. and the mixture was extracted with EtOAc (2 L+1 L). The organic layer was washed successively with 12% NaCl aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1) to afford ethyl (3-{3-[5-(diphenylmethyl)-2-oxo-1(2H) -pyridinyl]propyl}phenoxy)-acetate(113 g) as a slightly yellow oil.

후처리

  1. extractionthe mixture was extracted with EtOAc (2 L+1 L)
  2. washThe organic layer was washed successively with 12% NaCl aqueous solution and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1)

출처 및 근거

ORD 기록
ord-15612b04ce5c4cb2aa9877d8b0534770
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273745B2

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