p-Toluenesulfonic acid → Trans 4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane

HRID 481726

反応式

HRID 481726 の反応式
[CH2:1]([O:3][CH:4]([O:14][CH2:15][CH3:16])[CH2:5][P:6]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])=[O:7])C.[Br:17]CC(O)CO.CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:17][CH2:16][C@@H:15]1[CH2:1][O:3][C@@H:4]([CH2:5][P:6]([O:8][CH2:9][CH3:10])([O:11][CH2:12][CH3:13])=[O:7])[O:14]1

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 208273-Bromo-1,2-propanediolHCID 82071Diethyl (2,2-diethoxyethyl)phosphonateHCID 516892Sodium Bicarbonate

生成物 1

HCID 56632209Trans 4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane収率 96%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of diethylphosphonoacetaldehyde diethylacetal (15.00 g, 59.0 mmol) and 3-bromo-1,2-propanediol (11.00 g, 71.0 mmol, 1.2 eq.) in toluene (60 mL) was added pTSA (few cristals). The mixture was stirred at reflux for 72 hr and was cooled to room temperature. A saturated solution of sodium bicarbonate was added and the aqueous phase was extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude material was pure by TLC and NMR and gave 17.93 g of the compound in a 96% yield.

後処理

  1. temperatureat reflux for 72 hr
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-b19d7676639c47a1bba1f06f451fc4a6
出典データセット
uspto-grants-1998_08
特許番号
US05789394

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