Sodium hydride → HCID 18467792, compound

HRID 2229433Notes

Reaction equation

HRID 2229433 reaction equation
[C:1]([CH:3]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[CH2:4]1)#[N:2].[H-].[Na+].Br[CH2:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19]>CN(C)C=O>[C:1]([CH:3]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[CH:10][C:5]=2[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 12159643HCID 12159643, compound

Product 1

HCID 18467792HCID 18467792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 16.5 g of 1-cyano-4-hydroxybenzocyclobutane in 205 ml of dimethylformamide is poured into a suspension of 67.8 mmol of sodium hydride in 160 ml of dimethylformamide. The reaction mixture is stirred for 30 minutes and then a solution of 10.2 ml of 1-bromo-2,2-diethoxyethane in 40 ml is added over the course of 15 minutes and the temperature is then maintained at 60° C. for 6 hours. The mixture is stirred for a further 12 hours, the dimethylformamide is removed by evaporation, and the residue is taken up in water, extracted with dichloromethane, dried and concentrated in vacuo. The residue is chromatographed over silica gel (CH2Cl2/AcOEt: 95/5), enabling the expected product to be isolated.

Workup

  1. stirringThe mixture is stirred for a further 12 hours
  2. customthe dimethylformamide is removed by evaporation
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed over silica gel (CH2Cl2/AcOEt: 95/5)
  7. customto be isolated

Sources & evidence

ORD record
ord-5598f8bcec8d4e1fb7b875a1f1d8363b
Source dataset
uspto-grants-2002_07
Patent number
US06420413B2

Reaction notes

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