Isopropanol → trans 4-(Bromomethyl)-2-isopropoxy-1,3-dioxolane

HRID 636860ノート

反応式

HRID 636860 の反応式
[Br:1][CH2:2][C@@H:3]1[CH2:7][O:6][C@@H:5]([O:8]C)[O:4]1.C(O)(C)C.[C:14]1([CH3:24])[CH:19]=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][CH2:2][C@@H:3]1[CH2:7][O:6][C@@H:5]([O:8][CH:14]([CH3:19])[CH3:24])[O:4]1

参加物

5

反応物 3

HCID 3776Isopropanol2 回HCID 6101p-Toluenesulfonic acidHCID 86752979trans 4-(Bromomethyl)-2-methoxy-1,3-dioxolane

生成物 1

HCID 10944119trans 4-(Bromomethyl)-2-isopropoxy-1,3-dioxolane

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of cis and trans 4-(bromomethyl)-2-methoxy-1,3-dioxolane (example 1) (5.37 g, 27.3 mmol) in benzene (100 mL) was added isopropanol (2.2 mL, 28.6 mmol, 1.05 eq.) and p-toluenesulfonic acid (pTSA, few crystals). The mixture was stirred for 24 hr at 88°-90° C. followed by addition of isopropanol (0.5 mL, 0.24 eq.). The mixture was stirred for further 24 hr at 90° C., cooled to room temperature and benzene was removed under reduced pressure. The crude material was obtained in quantitative yield consisting of a mixture of isopropoxy and methoxy orthoesters in a 9:1 ratio respectively. The ratio of cis and trans isomers was about 1:1.

後処理

  1. stirringThe mixture was stirred for further 24 hr at 90° C.
  2. custombenzene was removed under reduced pressure

出典と根拠

ORDレコード
ord-8bb42e183d9f4a4cb0e49c402b07a7bb
出典データセット
uspto-grants-2001_02
特許番号
US06194576B1

反応ノート

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