Methanol → (1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol

HRID 2058139ノート

反応式

HRID 2058139 の反応式
[C:1]([CH:5]([CH3:21])[CH2:6][CH2:7][CH2:8][C:9]1([CH3:20])[CH:15]2[O:16][C:12]([CH2:17][CH2:18][OH:19])([CH2:13][CH2:14]2)[CH2:11][O:10]1)([O:3]C)=[O:2].CO.[OH-].[Na+]>O>[C:1]([CH:5]([CH3:21])[CH2:6][CH2:7][CH2:8][C:9]1([CH3:20])[CH:15]2[O:16][C:12]([CH2:17][CH2:18][OH:19])([CH2:13][CH2:14]2)[CH2:11][O:10]1)([OH:3])=[O:2]

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 23349561(1RS,4SR,5RS)-4-(4-carbomethoxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol

生成物 1

HCID 23349564(1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of (1RS,4SR,5RS)-4-(4-carbomethoxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol (71 mg, 0.24 mM), methanol (3 ml), water (1 ml) and 1 N sodium hydroxide (1 ml) is stirred at room temperature under nitrogen for twenty hours. Most of the methanol is removed in vacuo and the residue is treated with concentrated hydrochloric acid (1 ml) at 0° C. and extracted with ethyl acetate (3×30 ml). The combined organic layers are dried (Na2SO4) and evaporated in vacuo to give a colorless oil. This material is filtered through a silica gel column (3 g) and washed with ether (200 ml). The solvent is removed in vacuo to give (1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol (58 mg, 88%) as a colorless oil.

後処理

  1. customMost of the methanol is removed in vacuo
  2. additionthe residue is treated with concentrated hydrochloric acid (1 ml) at 0° C.
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customevaporated in vacuo
  6. customto give a colorless oil
  7. filtrationThis material is filtered through a silica gel column (3 g)
  8. washwashed with ether (200 ml)
  9. customThe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-bef1c103fb8f4659a5ec5bff95960d8a
出典データセット
uspto-grants-1980_07
特許番号
US04215048

反応ノート

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