Phenylacetonitrile → HCID 57794809, compound

HRID 2099265Notes

Reaction equation

HRID 2099265 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=CC(S(O[CH2:21][C@@H:22]([OH:32])[CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=O)=O)=CC=1.C([Li])CCC>C1COCC1.CCOC(C)=O>[OH:32][C@@H:22]([CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:21][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[N:9]

Participants

6

Reactant 3

HCID 8794PhenylacetonitrileHCID 136448701,2-Propanediol, 3-(phenylmethoxy)-, 1-(4-methylbenzenesulfonate), (2S)-HCID 178418339Butyllithium

Product 1

HCID 57794809HCID 57794809, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Phenylacetonitrile (4.59 g, 39.2 mmol) and (2S)-2-hydroxy-3-[(phenylmethyl)oxy]propyl 4-methylbenzenesulfonate (13.20 g, 39.2 mmol, 1 eq) were dissolved in 50 mL THF, cooled to −78° C., and treated with 2.5M butyllithium in hexanes (35 mL, 86.3 mmol, 2.2 eq) added dropwise over 30 min. The reaction mixture was stirred 4 h at −78° C., allowed to warm to ambient temperature and stirred an additional 16 h. The reaction mixture was diluted with EtOAc, washed successively with water and brine, dried over MgSO4, filtered and concentrated to give the diastereomeric product as an orange oil in quantitative yield which was carried on without purification. ES-LCMS m/z 304.33 (M+Na).

Workup

  1. additionadded dropwise over 30 min
  2. temperatureto warm to ambient temperature
  3. stirringstirred an additional 16 h
  4. washwashed successively with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82fb809f4fd145c5a80ffc4d4629726e
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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