Sodium Hydroxide → HCID 69357347, compound

HRID 1271254Notes

Reaction equation

HRID 1271254 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][OH:12].[OH-].[Na+].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]/[CH:10]=[CH: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 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 10975949(Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-ol

Product 1

HCID 69357347HCID 69357347, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

6.00 g of (Z)-4-(2-tetrahydropyranyloxy)-2-buten-1-ol was dissolved in 10 ml of benzene and 1.18 g of tetra-n-butylammonium hydrogen sulfate and 10 ml of an aqueous 50% sodium hydroxide solution were added and 6.75 ml of tert-butyl bromoacetate was added dropwise while stirring under ice cooling. After 10 minutes, the temperature was returned to room temperature and the reaction solution was stirred for one hour. The solution was extracted with diethyl ether after adding ice water. The extract was washed with saturated brine and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.00 g of the desired compound as a colorless oily substance.

Workup

  1. customwas returned to room temperature
  2. stirringthe reaction solution was stirred for one hour
  3. extractionThe solution was extracted with diethyl ether
  4. additionafter adding ice water
  5. washThe extract was washed with saturated brine
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-10135a26e3c44d4d9593e6b217a1d450
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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