Acetonitrile → HCID 54534630, compound

HRID 461996Notes

Reaction equation

HRID 461996 reaction equation
[C:1](#[N:3])C.[O:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].[CH3:14][CH2:15][CH2:16]CCC>>[OH:4][CH:8]([CH:7]1[CH:15]2[CH2:16][CH:9]3[CH2:10][CH:11]([CH2:12][CH:6]1[CH2:5]3)[CH2:14]2)[C:1]#[N:3]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8028Tetrahydrofuran2×HCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 54534630HCID 54534630, compound

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 butyl lithium, 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 five minutes and 0.1 mole adamant-2-one 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 separated and dried with anhydrous magnesium sulfate and filterd. The filtrate is evaporated to dryness, under vacuum, affording 2-hydroxy-2-(adamant-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. customThe organic layer is separated
  8. dry with materialdried with anhydrous magnesium sulfate and filterd
  9. customThe filtrate is evaporated to dryness, under vacuum

Sources & evidence

ORD record
ord-37cf18ec53474041b43bc7d902239cdf
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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