Glycolaldehyde → 2-(2,2-Dimethylmorpholino)ethanol

HRID 601563Notes

Reaction equation

HRID 601563 reaction equation
[CH3:1][C:2]1([CH3:8])[O:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH:9](=O)[CH2:10][OH:11].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH3:1][C:2]1([CH3:8])[O:7][CH2:6][CH2:5][N:4]([CH2:9][CH2:10][OH:11])[CH2:3]1

Participants

5

Reactant 3

HCID 756GlycolaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 189596742,2-Dimethylmorpholine

Product 1

HCID 129508532-(2,2-Dimethylmorpholino)ethanol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Dissolve 2,2-dimethylmorpholine (151 mg, 1.0 mmol) in 1,2-dichloroethane (3 mL) and add glycolaldehyde (60 mg, 1.0 mmol). Stir at room temperature for 30 min followed by addition of NaBH(OAc)3 (233 mg, 1.1 mmol). Stir 3 h, then quench by adding 30 mL of 1N NaOH. Pour into a separatory funnel and extract with EtOAc (2×50 mL). Wash the combined organic layers with brine (50 mL). The crude alcohol was used as is without further purification. MS (ES+) 160.2 (M+1)+.

Workup

  1. stirringStir 3 h
  2. customquench
  3. additionby adding 30 mL of 1N NaOH
  4. additionPour into a separatory funnel
  5. extractionextract with EtOAc (2×50 mL)
  6. washWash the combined organic layers with brine (50 mL)
  7. customas is without further purification

Sources & evidence

ORD record
ord-fa6bbe474ff643aa961d25cd3b9eca21
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

Loading…