Acetonitrile → HCID 69477576, compound

HRID 1034964Notes

Reaction equation

HRID 1034964 reaction equation
[C:1](#[N:3])[CH3:2].[CH2:4]([Li])[CH2:5][CH2:6][CH3:7].C([O:16][C:17]([N:19]([CH2:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=1)[C:33]([O:35]C)=O)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:18])C1C=CC=CC=1.O1C[CH2:43][CH2:42][CH2:41]1>>[CH2:4]([O:16][C:17](=[O:18])[N:19]([CH2:29][C:30]1[CH:39]=[CH:38][CH:37]=[C:32]([C:33](=[O:35])[CH2:2][C:1]#[N:3])[CH:31]=1)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:5]1[CH:43]=[CH:42][CH:41]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8028Tetrahydrofuran2×HCID 69161966HCID 69161966, compoundHCID 178418339Butyllithium

Product 1

HCID 69477576HCID 69477576, compoundYield 96%

Conditions

Temperature
-78 °C

Procedure

A solution of acetonitrile (1.46, 28 mmol) in tetrahydrofuran (180 mL) was treated with n-butyl lithium (1.6 M solution in hexane, 14 mL, 22.2 mmol) at −78° C. for 10 minutes. A solution of EXAMPLE 56B (7.8 g, 18.6 mmol) in 40 mL of tetrahydrofuran was added and the mixture stirred at −78° C. for 1 hour and at ambient temperature for 1 hour. After quenching with water, the mixture was acidified with 2N hydrochloric acid to a pH of 3. The mixture was partitioned between ethyl acetate and brine and the organic phase washed with water and concentrated. The residue was purified by flash chromatography on silica gel using 30% ethyl acetate in hexane to give 7.7 g (96%) of the title compound. MS (DCI): m/z 429 (M+H)+.

Workup

  1. customAfter quenching with water
  2. customThe mixture was partitioned between ethyl acetate and brine
  3. washthe organic phase washed with water
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel using 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9a28cc9a62f2460984b3372074ea565f
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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