Potassium Hydroxide → 2-[4-(2-tetrahydropyranyloxy)butyloxy]acetic Acid Tert-Butyl Ester

HRID 1271248Notes

Reaction equation

HRID 1271248 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[OH-].[K+].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:20]([O:19][C:17](=[O:18])[CH2:16][O:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 79177tert-Butyl bromoacetateHCID 5591134-(Tetrahydro-2H-pyran-2-yloxy)-1-butanol

Product 1

HCID 693544612-[4-(2-tetrahydropyranyloxy)butyloxy]acetic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

35.98 g of 4-(2-tetrahydropyranyloxy)-1-butanol was dissolved in 300 ml of benzene and then 33.95 g of tetra-n-butylammonium hydrogen sulfate and 300 ml of an aqueous 40% potassium hydroxide solution were added. While stirring vigorously under ice cooling, 10.5 ml of tert-butyl bromoacetate was added dropwise so as to control the inner temperature to 5 to 10° C. or lower. After stirring for 45 minutes, an ice bath was removed and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with water and then extracted with diethyl ether. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 36.21 g of the desired compound as a colorless oily substance.

Workup

  1. customto 5 to 10° C.
  2. stirringAfter stirring for 45 minutes
  3. customan ice bath was removed
  4. stirringthe mixture was stirred at room temperature for one hour
  5. additionThe reaction solution was diluted with water
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2fe714d860954d8b823909a7b85566be
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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