Acetonitrile → HCID 14769837, compound

HRID 2351853Notes

Reaction equation

HRID 2351853 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19](#[N:21])[CH3:20]>O1CCCC1>[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH2:20][C:19]#[N:21])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 14559668Ethyl 4-(phenylmethoxy)butanoate

Product 1

HCID 14769837HCID 14769837, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a stream of argon, 248 ml of tetrahydrofuran was added to 26 g (0.65 mole) of 60% sodium hydride, and a solution of 72.2 g (0.325 moles) of ethyl 4-benzyloxybutyrate and 26.7 g (0.65 mole) of acetonitrile in 94 ml of anhydrous tetrahydrofuran was added dropwise over the course of 40 minutes, and the mixture was heated under reflux for 2.5 hours. After cooling, the reaction mixture was poured into ice water, and washed with a 1:1 mixture of hexane and ether. The aqueous layer was acidified with concentrated hydrochloric acid, and extracted with ether. The ether layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting crude 6-benzyloxy-3-ketohexanenitrile was subjected to silica gel column chromatography. The column was eluted with a 1:1 mixture of hexane and ether to give 57.8 g (81.2%) of a pale yellow oily product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureAfter cooling
  4. washwashed with a 1:1 mixture of hexane and ether
  5. extractionextracted with ether
  6. washThe ether layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. washThe column was eluted with a 1:1 mixture of hexane and ether

Sources & evidence

ORD record
ord-483b023fc34347c3b72957b98d4b16ce
Source dataset
uspto-grants-1989_10
Patent number
US04874760

Reaction notes

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