Butan-1-olate → Ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-9-decenoate

HRID 1792410노트

반응식

HRID 1792410 반응식
[F:1][C:2]([F:17])([C:13]([F:16])([F:15])[F:14])[CH2:3][CH2:4][C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[O-]CCCC.I[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31]>C1COCC1.[K]>[F:1][C:2]([F:17])([C:13]([F:14])([F:15])[F:16])[CH2:3][CH2:4][C:5]([CH:6]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=[CH2:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:12]

참가 물질

6

반응물 3

HCID 12476378Butan-1-olateHCID 138898108-Iodooct-1-eneHCID 22033121Ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate

생성물 1

HCID 22033009Ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-9-decenoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 5462222Potassium용매

실험 절차

To a stirred solution of ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate (262 mg, 1 mmol) in anhydrous THF (4 ml), potassium tret-butoxide (112 mg, 1 mmol) was added as a solid and the mixture was stirred at room temperature for 30 min. Then to a solution of 8-iodo-1-octene (357 mg, 1.5 mmol) in anhydrous THF (1 ml) was added and the mixture was stirred at room temperature continued for 3 days. The mixture was concentrated, diluted with diethyl ether, washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuum. Crude product was purified by flash chromatography on silica gel (hexane:ethyl acetate 10:1) to give ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-9-decenoate as a colorless oil. yield: 200 mg (54%).

후처리

  1. additionwas added as a solid
  2. stirringthe mixture was stirred at room temperature
  3. waitcontinued for 3 days
  4. concentrationThe mixture was concentrated
  5. additiondiluted with diethyl ether
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuum
  9. customCrude product was purified by flash chromatography on silica gel (hexane:ethyl acetate 10:1)

출처 및 근거

ORD 기록
ord-126b46c583eb4d38b98c533b7ad86f3c
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

반응 노트

불러오는 중…