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Hydrochloric Acid → 4-Fluorophenyldiphenylsulfonium 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate

HRID 1506743
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HRID 1506743 반응식
[C:1]12([CH:11]([OH:20])[C:12]([F:19])([F:18])[C:13]([O:15]CC)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+].Cl.[Cl-].[F:25][C:26]1[CH:31]=[CH:30][C:29]([S+:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1>C(Cl)Cl.O.O1CCOCC1>[C:1]12([CH:11]([OH:20])[C:12]([F:19])([F:18])[C:13]([O-:15])=[O:14])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2.[F:25][C:26]1[CH:31]=[CH:30][C:29]([S+:32]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866496604-Fluorophenyldiphenylsulfonium chlorideHCID 117966659Ethyl 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate

생성물 1

HCID 1317343644-Fluorophenyldiphenylsulfonium 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate수율 57%

시약·촉매·용매 3

HCID 962Water용매
HCID 6344Dichloromethane용매
HCID 312751,4-Dioxane용매

실험 절차

A mixture of 6.6 g of ethyl 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate, prepared in Synthesis Example 1-11, 50 g of 1,4-dioxane, 8.0 g of 25 wt % sodium hydroxide, and 20 g of water was stirred for 2 hours. To the reaction solution, 2.0 g of 35 wt % hydrochloric acid was added, and then 53 g of an aqueous solution of 4-fluorophenyldiphenylsulfonium chloride and 100 g of methylene chloride were added. After stirring for 30 minutes, the organic layer was taken out, washed with water, and concentrated under reduced pressure. Methyl isobutyl ketone was added to the concentrate, which was concentrated again. Diisopropyl ether was added to the concentrate for crystallization. The resulting solid was dried in vacuum, obtaining 6.2 g of the target compound, 4-fluorophenyldiphenylsulfonium 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate as white crystals (yield 57%).

후처리

  1. stirringAfter stirring for 30 minutes
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure
  4. additionMethyl isobutyl ketone was added to the concentrate, which
  5. concentrationwas concentrated again
  6. additionDiisopropyl ether was added to the
  7. concentrationconcentrate for crystallization
  8. customThe resulting solid was dried in vacuum

출처 및 근거

ORD 기록
ord-6e9c65a5045c4f4c8000bac583fea248
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221742B2

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