Tetrahydrofuran → 2-(4-Methylbutyloxy)acetaldehyde diethylacetal

HRID 1769427

Reaction equation

HRID 1769427 reaction equation
C[C@H:2]([OH:6])[CH2:3][CH2:4][CH3:5].[H-].[Na+].[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13]Br)[CH3:10].O1CCC[CH2:19]1>>[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13][O:6][CH2:2][CH2:3][CH2:4][CH2:5][CH3:19])[CH3:10]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 2724896(+)-2-Pentanol

Product 1

HCID 199306252-(4-Methylbutyloxy)acetaldehyde diethylacetal

Procedure

35 g of (S)-2-pentanol was dissolved in tetrahydrofuran, and 16 g of 60 % sodium hydride was added thereto. After stirring for 30 minutes, 80 g of bromoacetaldehyde diethylacetal was added thereto, and the mixture was refluxed for 6 hours. After the reaction solution was concentrated and water and ether were added thereto, the mixture was shaken for mixing. The organic layer was collected and was dried with magnesium sulfate to remove the solvent off. Purification was carried out by column chromatography to obtain 2-(4-methylbutyloxy)acetaldehyde diethylacetal (54).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. concentrationAfter the reaction solution was concentrated
  3. additionwater and ether were added
  4. stirringthe mixture was shaken
  5. additionfor mixing
  6. customThe organic layer was collected
  7. dry with materialwas dried with magnesium sulfate
  8. customto remove the solvent off
  9. customPurification

Sources & evidence

ORD record
ord-3557c6b09319466facd659160f7875ef
Source dataset
uspto-grants-1995_01
Patent number
US05380915

Linked notes

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