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2,2,2-Cryptand → 2-[2-(2-Fluoromethyl-phenylsulfanyl)-ethyl]-[1,3]dioxolane

HRID 217555
ノート
印刷プレビュー

反応式

HRID 217555 の反応式
[F-:1].[K+].C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.Cl[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37][CH2:38][CH2:39][CH:40]1[O:44][CH2:43][CH2:42][O:41]1>C(#N)C>[F:1][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37][CH2:38][CH2:39][CH:40]1[O:44][CH2:43][CH2:42][O:41]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 585188932-[2-(2-Chloromethyl-phenylsulfanyl)-ethyl]-[1,3]dioxolane

生成物 1

HCID 585188752-[2-(2-Fluoromethyl-phenylsulfanyl)-ethyl]-[1,3]dioxolane

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Potassium fluoride (3.5 mg, 0.060 mmol) and kryptofix 222 (22.5 mg, 0.060 mmol) were dissolved in acetonitrile (1 ml) and added to 2-[2-(2-chloromethyl-phenylsulfanyl)-ethyl]-[1,3]dioxolane (7.7 mg, 0.030 mmol) in acetonitrile (1 ml). The reaction mixture was heated to 70 degrees for 30 minutes. The crude product was purified by reverse phase preparative chromatography (Vydac 218TP1022 column; solvents A=water/0.1% TFA and B=CH3CN/0.1% TFA; gradient 40-80% B over 40 min; flow 10 ml/minute; detection at 254 nm). The fractions were left in the fridge overnight and to the acetonitrile phase was added diethyl ether, dried (Na2SO4) and evaporated under reduced pressure. (Analytical HPLC: Vydac 218TP54 column; solvents: A=water/0.1% TFA and B=CH3CN/0.1% TFA; gradient 40-80% B over 20 min; flow 1.0 ml/minute; retention time 9.200 minutes detected at 214 and 254 nm). Structure verified by NMR.

後処理

  1. temperatureThe reaction mixture was heated to 70 degrees for 30 minutes
  2. customThe crude product was purified by reverse phase preparative chromatography (Vydac 218TP1022 column; solvents A=water/0.1% TFA and B=CH3CN/0.1% TFA; gradient 40-80% B over 40 min; flow 10 ml/minute; detection at 254 nm)
  3. additionwas added diethyl ether
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. waitgradient 40-80% B over 20 min

出典と根拠

ORDレコード
ord-35735f1d33d54c8ab1e2ca5bd46efe7c
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08197793B2

反応ノート

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