Acetic Acid → 4-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-penten-1-ol

HRID 4462

반응식

HRID 4462 반응식
[Br:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:23]=[CH:22][C:10]([O:11][CH:12]([CH3:21])[C:13]([O:19][CH3:20])=[CH:14][C:15](OC)=[O:16])=[CH:9][CH:8]=2)=[C:4]([F:26])[CH:3]=1.CC(C[AlH]CC(C)C)C.CCOCC.C(O)(=O)C>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:23]=[CH:22][C:10]([O:11][CH:12]([CH3:21])[C:13]([O:19][CH3:20])=[CH:14][CH2:15][OH:16])=[CH:9][CH:8]=2)=[C:4]([F:26])[CH:3]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydrideHCID 867419984-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl ester

생성물 1

HCID 543727674-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-penten-1-ol수율 74%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of 4.5 g (10.6 mmol) 4-(4-(4-bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl ester in 25 ml toluene at -78° C. was added dropwise over a period of 30 min, 16.5 ml of 1.5M DIBAL-H in toluene, keeping the temperature below -60° C. The mixture was stirred for 21/2 hours at -78° C. To the mixture was added 17 ml of a 75:25:6 ether:acetic acid:water mixture, keeping the temperature below -60° C. The mixture was then allowed to warm to room temperature and the solid material was filtered off. The filtrate was washed twice with saturated NaHCO3 and once with water, dried over MgSO4 and the solvent was removed by rotary evaporation. The residue was purified by HPLC, eluting with 80:20 hexane:acetone, to give 3.1 g (74%) of the product as a pale yellow oil which was used immediately in the next reaction.

후처리

  1. customthe temperature below -60° C
  2. customthe temperature below -60° C
  3. temperatureto warm to room temperature
  4. filtrationthe solid material was filtered off
  5. washThe filtrate was washed twice with saturated NaHCO3 and once with water
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed by rotary evaporation
  8. customThe residue was purified by HPLC
  9. washeluting with 80:20 hexane

출처 및 근거

ORD 기록
ord-06486a43573049c0972d0737d58446eb
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725683

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