Water → 2-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-propyloxy)tetrahydropyran

HRID 863563Notes

Reaction equation

HRID 863563 reaction equation
[NH2-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][CH2:11][CH2:12][C:13]1(C#N)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][CH2:16][C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]1=2.O>C1(C)C=CC=CC=1>[CH:24]1[C:15]2[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:13]([CH2:12][CH2:11][CH2:10][O:9][CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8][O:3]3)[C:14]=2[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24533Sodium amideHCID 187993365-(3-(tetrahydropyran-2-yloxy)-1propyl)-10,11dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile

Product 1

HCID 187993162-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-propyloxy)tetrahydropyranYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under nitrogen, sodium amide (3.5 g, 0.045 mol, 50% suspension in toluene) was added to a 100 ml three-necked roundbottom flask. The above nitrile (4.0 g, 0.011 mol) was dissolved in dry toluene (50 ml) and added. The reaction mixture was heated at reflux temperature for 16 h. After cooling to room temperature, water was added with caution (100 ml). More toluene was added and the organic phase was washed with dilute HCl. After drying (MgSO4), the organic phase was evaporated in vacuo affording 3.0 g (81%) of crude 2-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-propyloxy)tetrahydropyran as an oil.

Workup

  1. additionadded
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux temperature for 16 h
  4. washthe organic phase was washed with dilute HCl
  5. dry with materialAfter drying (MgSO4)
  6. customthe organic phase was evaporated in vacuo

Sources & evidence

ORD record
ord-0e066211281e4759bcc41293e98fd1be
Source dataset
uspto-grants-1998_02
Patent number
US05721254

Reaction notes

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