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

HRID 481727

反応式

HRID 481727 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]C[C@H](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 82071Diethyl (2,2-diethoxyethyl)phosphonateHCID 516892Sodium BicarbonateHCID 2733893(2R)-3-Bromo-1,2-propanediol

生成物 1

HCID 53652584(2S,4R)-4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane収率 97%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of diethylphosphonoacetaldehyde diethylacetal (4.20 g, 16.5 mmol) and (2R)-3-bromo-1,2-propanediol (example 90) (3.00 g, 19.4 mmol, 1.2 eq.) in toluene (30 mL) was added pTSA (few crystals). The mixture was stirred at reflux for 50 hr. After, the solution was cooled to room temperature, and a saturated solution of sodium bicarbonate was added, and the aqueous phase was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude material was pure by TLC and NMR, and gave 5.06 g of the compound in a 97% yield.

後処理

  1. temperatureat reflux for 50 hr
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-7bbdeea3b5be4a31b4ecdd53736db2cf
出典データセット
uspto-grants-1998_08
特許番号
US05789394

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