Lithium hydroxide, monohydrate → 5-Vinyl[1,3]dioxane-5-carboxylic acid

HRID 2176247Notes

Reaction equation

HRID 2176247 reaction equation
C([O:3][C:4]([C:6]1([CH:12]=[CH2:13])[CH2:11][O:10][CH2:9][O:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+]>O1CCCC1.CO.O>[CH:12]([C:6]1([C:4]([OH:5])=[O:3])[CH2:7][O:8][CH2:9][O:10][CH2:11]1)=[CH2:13]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 85877288Ethyl 5-vinyl-1,3-dioxane-5-carboxylate

Product 1

HCID 867060855-Vinyl[1,3]dioxane-5-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 5-vinyl-[1,3]dioxane-5-carboxylic acid ethyl ester (397.7 mg, 2.136 mmol) in tetrahydrofuran/methanol/water (15 mL, 2:2:1) was treated with lithium hydroxide monohydrate (269 mg, 6.408 mmol). After stirring at room temperature for 1.5 h, the volatiles were removed in vacuo and the residue was cooled to 0° C. and quenched with hydrochloric acid (1 M). The aqueous layer was saturated with sodium chloride, extracted with dichloromethane (3×). The combined organics were filtered through a phase separator and the volatiles were removed in vacuo to provide the title compound (320.3 mg, 95%) as a colourless solid. 1H NMR (300 MHz, CDCl3) δ 3.72 (d, J=11.6 Hz, 2H), 4.50 (d, J=11.4 Hz, 2H), 4.73 (d, J=6.2 Hz, 1H), 5.02 (d, J=6.0 Hz, 1H), 5.27-5.39 (m, 2H), 5.69 (dd, J=17.6, 10.9 Hz, 1H).

Workup

  1. customthe volatiles were removed in vacuo
  2. temperaturethe residue was cooled to 0° C.
  3. customquenched with hydrochloric acid (1 M)
  4. extractionextracted with dichloromethane (3×)
  5. filtrationThe combined organics were filtered through a phase separator
  6. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-a6159cf9d60f4af9b1cac0954ee00ffe
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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