Acetonitrile → HCID 20081759, compound

HRID 274928Notes

Reaction equation

HRID 274928 reaction equation
[C:1]([CH:5]([C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)[O:6][C:7]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:10]([CH2:11]O)=[CH:9][C:8]=1[CH2:18][CH2:19][CH3:20])([O:3][CH3:4])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:50].CC#N>C1COCC1>[C:1]([CH:5]([C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)[O:6][C:7]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:10]([CH2:11][Br:50])=[CH:9][C:8]=1[CH2:18][CH2:19][CH3:20])([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20081760HCID 20081760, compound

Product 1

HCID 20081759HCID 20081759, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step B (0.53 g, 1.38 mmol) in dry THF (10 mL) were added Ph3P (0.49 g, 2.06 mmol), CBr4 (0.69 g, 2.06 mmol) and CH3CN (2 mL), and the mixture was stirred at room temperature for 14 h. At the end of this period, the reaction mixture was concentrated in vacuo to provide an oil, which was then purified by flash chromatography on silica-gel using ethyl acetate-hexane (1:9) to provide the titled product as a thick colorless oil (0.57 g).

Workup

  1. concentrationAt the end of this period, the reaction mixture was concentrated in vacuo
  2. customto provide an oil, which
  3. customwas then purified by flash chromatography on silica-gel

Sources & evidence

ORD record
ord-8710541ba6df4271b1deba4f287eeeef
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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