Water → HCID 86752907, compound

HRID 1956563Notes

Reaction equation

HRID 1956563 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]2[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:27](Br)[C:28]#[CH:29].O>CN(C)C=O.[Cl-].[Na+].O.COC(C)(C)C>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:8][C:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]2[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=2[CH:10]=1)[CH2:29][C:28]#[CH:27])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 85700546HCID 85700546, compound

Product 1

HCID 86752907HCID 86752907, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

1.0 g (3.091 mmol) of dibenz[b,f]oxepin-10-ylmethyl-carbamic acid tert-butyl ester is placed in 10 ml of dimethylformamide, 0.22 g (4.636 mmol) of 55% sodium hydride suspension (in oil) is added at room temperature, the mixture is stirred for 15 minutes and then 0.279 ml (3.709 mmol) of propargyl bromide is added dropwise at room temperature. After 1 hour, water and a small amount of brine are carefully added and tert-butyl methyl ether is mixed in. The organic phase is washed 4× with water, dried over sodium sulfate and concentrated. 1.106 g (3.06 mmol)=98.8% of dibenz[b,f]oxepin-10-ylmethyl-prop-2-ynyl-carbamic acid tert-butyl ester are obtained in the form of a brown oil. TLC (silica gel, ethyl acetate/hexane=9:1; UV): Rf =0.45.

Workup

  1. waitAfter 1 hour
  2. washThe organic phase is washed 4× with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f5eeac3ffb541caa320a85e78c7d7a4
Source dataset
uspto-grants-1998_07
Patent number
US05780500

Reaction notes

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