Acetonitrile → HCID 21392664, compound

HRID 461982Notes

Reaction equation

HRID 461982 reaction equation
[C:1](#[N:3])[CH3:2].[O:4]1CCCC1.C([Li])CCC.[CH:14]12[CH2:19][CH:18]1[CH2:17][CH2:16][C:15]2=O>CCCCCC>[OH:4][CH:2]([CH:15]1[CH2:16][CH2:17][CH:18]2[CH:14]1[CH2:19]2)[C:1]#[N:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028Tetrahydrofuran2×HCID 549294Bicyclo[3.1.0]hexan-2-oneHCID 178418339Butyllithium

Product 1

HCID 21392664HCID 21392664, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In this preparation 10 ml. of acetonitrile is stirred in 300 ml. of anhydrous tetrahydrofuran, under nitrogen, and cooled to -70° C. 62.5 Ml. (0.1 mole) of 1.6 M butyllithium, in hexane, is added dropwise at a controlled rate such that the temperature of the mixture does not exceed -50° C. The mixture is then stirred for 5 minutes and 0.1 mole of bicyclo[3.1.0]hexan-2-one (J. Org. Chem., v. 22, 1146 (1957)) in 60 ml. of anhydrous tetrahydrofuran is added dropwise and the mixture then allowed to warm to room temperature. The mixture is then evaporated, under vacuum, to remove the tetrahydrofuran solvent and then 300 ml. of ethyl acetate is added and the mixture washed twice with water. The organic layer is dried with anhydrous magnesium sulfate and filtered. The filtrate is evaporated to dryness, under vacuum, affording 2-hydroxy-2-(bicyclo[3.1.0]hex-2-yl)acetonitrile.

Workup

  1. customIn this preparation 10 ml
  2. customdoes not exceed -50° C
  3. customThe mixture is then evaporated, under vacuum
  4. customto remove the tetrahydrofuran solvent
  5. additionof ethyl acetate is added
  6. washthe mixture washed twice with water
  7. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate is evaporated to dryness, under vacuum

Sources & evidence

ORD record
ord-77aeaa1d86114fa6b0adcd73683f55e8
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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