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

HRID 1506743
ノート
印刷プレビュー

反応式

HRID 1506743 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6344Dichloromethane溶媒
HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6e9c65a5045c4f4c8000bac583fea248
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09221742B2

反応ノート

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