Sodium Hydroxide → HCID 22910574, compound

HRID 1378267Notes

Reaction equation

HRID 1378267 reaction equation
[CH:1](/[CH:5]1[CH2:10][O:9][CH:8]([CH2:11][CH2:12][CH:13]([C:19](OCC)=[O:20])[C:14](OCC)=[O:15])[O:7][CH2:6]1)=[CH:2]\[CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH:1](/[CH:5]1[CH2:6][O:7][CH:8]([CH2:11][CH2:12][CH:13]([CH2:14][OH:15])[CH2:19][OH:20])[O:9][CH2:10]1)=[CH:2]\[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70188239HCID 70188239, compound

Product 1

HCID 22910574HCID 22910574, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 16.75 g of diethyl (E)-[2-(5-but-1-enyl-1,3-dioxan-2-yl)-ethyl]-malonate in 25 ml of tetrahydrofuran was added dropwise at 5°-8° C. under a protective gas to a suspension of 3.87 g of lithium aluminium hydride in 100 ml of tetrahydrofuran. The reaction mixture was stirred at 5° C. for a further 15 minutes, then at room temperature for 2 hours and finally at the boiling temperature for 1.2 hours. After cooling 3N sodium hydroxide solution was cautiously added dropwise until a solid white clump formed. The solution was decanted and the residue was washed twice with diethyl ether. The organic phases were combined, washed in succession with 25 ml of concentrated sodium bicarbonate solution and twice with 25 ml of concentrated sodium chloride solution each time, dried over sodium sulfate, filtered and the filtrate was concentrated. 12.20 g of crude (E)-2-[2-(5-but-1-enyl-1,3-dioxan-2-yl)-ethyl]-1,3-propanediol were obtained as a sticky-solid crude product, m.p. up to 87.1° C. (GC purity 86%, trans/cis ratio 7:3), which was used in the final step without further purification.

Workup

  1. waitat room temperature for 2 hours
  2. waitfinally at the boiling temperature for 1.2 hours
  3. additionwas cautiously added dropwise until a solid white clump
  4. customformed
  5. customThe solution was decanted
  6. washthe residue was washed twice with diethyl ether
  7. washwashed in succession with 25 ml of concentrated sodium bicarbonate solution and twice with 25 ml of concentrated sodium chloride solution each time
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-574f0392ed074547a563802e4ce494a1
Source dataset
uspto-grants-1997_09
Patent number
US05667721

Reaction notes

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