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

HRID 2058139Notes

Reaction equation

HRID 2058139 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bef1c103fb8f4659a5ec5bff95960d8a
Source dataset
uspto-grants-1980_07
Patent number
US04215048

Reaction notes

Loading…