Tetrahydrofuran → HCID 22033756, compound

HRID 1791983Notes

Reaction equation

HRID 1791983 reaction equation
O1CCCC1.[CH2:6]([O:8][CH:9]([O:15][CH2:16][CH3:17])[C:10]1([CH:13]=[O:14])[CH2:12][CH2:11]1)[CH3:7].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[CH2:16]([O:15][CH:9]([O:8][CH2:6][CH3:7])[C:10]1([CH2:13][OH:14])[CH2:11][CH2:12]1)[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 98555951-(Diethoxymethyl)cyclopropane-1-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 22033756HCID 22033756, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A tetrahydrofuran (190 mL) solution of 1-(diethoxymethyl)cyclopropane carboaldehyde (37.78 g) was cooled to 0° C. Lithium aluminum hydride (2 g, 52.7 mmol) was added and the mixture was stirred for 40 minutes. Water was added to terminate the reaction, followed by extraction with chloroform. The organic layer was washed with water and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby 34.60 g (91%) of the title compound was obtained as a colorless oil.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f2ffe11e5c51412598898fc7c32ee761
Source dataset
uspto-grants-2006_07
Patent number
US07074837B2

Reaction notes

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