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

HRID 2058139노트

반응식

HRID 2058139 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bef1c103fb8f4659a5ec5bff95960d8a
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04215048

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