2-(Benzyloxy) ethanol → Butyl[2-(benzyloxy)ethoxy]acetate

HRID 468599Notes

Reaction equation

HRID 468599 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]([O-])(C)C.[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])(C)C)=[O:21]>CC(O)(C)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:26][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 121412-(Benzyloxy) ethanolHCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 131731128Butyl[2-(benzyloxy)ethoxy]acetateYield 59%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of 2-(benzyloxy)ethanol 8 (1.7 g, 11.17 mmol) in t-BuOH (25 ml) was added at room temperature t-BuOK (1.38 g, 12.29 mmol). Mixture was stirred at room temperature for 2.5 hrs. t-butyl bromoacetate (2.7 ml, 20.11 mmol) was then added while mixture was cooled with a water bath. Mixture was stirred overnight at room temperature and concentrated. Water was added and aqueous layer was extracted with dichloromethane. Combined organic layers were dried over MgSO4, filtered and concentrated. Flash chromatography on silica gel (EtOAc/pentane 1/4) afforded ester 9 as an oil (1.749 g, 59%).

Workup

  1. temperaturewas cooled with a water bath
  2. stirringMixture was stirred overnight at room temperature
  3. concentrationconcentrated
  4. additionWater was added
  5. extractionaqueous layer was extracted with dichloromethane
  6. dry with materialCombined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-470c502833024ccea430f62d0a20702e
Source dataset
uspto-grants-2014_01
Patent number
US08624044B2

Reaction notes

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