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

HRID 4462

反応式

HRID 4462 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-06486a43573049c0972d0737d58446eb
出典データセット
uspto-grants-1988_02
特許番号
US04725683

関連ノート

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