Diethanolamine hydrochloride → 1-(2-iso-Propoxytetrahydro-3-furanyl)-1,2-ethanediol

HRID 1692155Notes

Reaction equation

HRID 1692155 reaction equation
[BH4-].[Na+].[OH:3][CH:4]([CH:10]1[CH2:14][CH2:13][O:12][CH:11]1[O:15][CH:16]([CH3:18])[CH3:17])[C:5](OCC)=[O:6].Cl.N(CCO)CCO>C(O)C.O>[CH:16]([O:15][CH:11]1[CH:10]([CH:4]([OH:3])[CH2:5][OH:6])[CH2:14][CH2:13][O:12]1)([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 518946Diethanolamine hydrochlorideHCID 4311764Sodium borohydrideHCID 25242000Ethyl hydroxy-(2-isopropoxytetrahydro-3-furanyl)acetate

Product 1

HCID 252420011-(2-iso-Propoxytetrahydro-3-furanyl)-1,2-ethanediol

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

In a 2 L round bottom flask charged with 600 mL of ethanol and NaBH4 (12.55 g, 0.33 mol, 1.1 eq.) at 0° C., ethyl hydroxy-(2-isopropoxytetrahydro-3-furanyl)acetate (70 g, 0.3 mol, 1 eq.) dissolved in 400 mL of ethanol was added dropwise over 1 hour at 0° C. The mixture was allowed to warm up at room temperature and stirred for 19 hours. After cooling at 0° C., diethanolamine hydrochloride (46.7 g, 0.33 mol, 1.1 eq.) dissolved in 100 mL of water was added over 10 min. and stirred for 8 hours. The solvent was evaporated under reduced pressure to afford a clear yellow solid. After dilution with 300 mL of ethylacetate, the heterogeneous mixture was filtered over dicalite. The mixture was used directly in the next step.

Workup

  1. additionwas added dropwise over 1 hour at 0° C
  2. temperatureAfter cooling at 0° C.
  3. additionwas added over 10 min.
  4. stirringstirred for 8 hours
  5. customThe solvent was evaporated under reduced pressure
  6. customto afford a clear yellow solid
  7. filtrationAfter dilution with 300 mL of ethylacetate, the heterogeneous mixture was filtered over dicalite

Sources & evidence

ORD record
ord-b018d2d89a6b4f599925463454d95fb8
Source dataset
uspto-grants-2012_04
Patent number
US08153829B2

Reaction notes

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