Tetrahydrofuran → HCID 57994322, compound

HRID 1009978Notes

Reaction equation

HRID 1009978 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].O1CCCC1>O1CCCC1.O.CCCCCCC>[CH2:19]([O:18][C:16](=[O:17])[NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 974724-HydroxybenzylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 57994322HCID 57994322, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 8900HeptaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-aminomethylphenol (1 g, 8.13 mmol) in tetrahydrofuran/water (1:1 ratio, 20 ml) at 0° C. was added solid NaHCO3 (0.888 g, 10.16 mmol) followed by dropwise addition of benzyl chloroformate (1.16 ml, 8.13 mmol). The mixture was stirred at 0° C. for 10 minutes then allowed to warm slowly to r.t. After stirring the mixture for 90 minutes the tetrahydrofuran was removed in vacuo. The aqueous layer was extracted with EtOAc (2×10 ml). The organic layer was washed with water (2×10 ml), dried (MgSO4), and the solvent removed in vacuo to a residue. Trituration with heptane gave the product as a white solid (2.10 g, 100% yield). LCMS purity 100%, m/z 258 [M++H]−.

Workup

  1. temperatureto warm slowly to r.t
  2. customwas removed in vacuo
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 ml)
  4. washThe organic layer was washed with water (2×10 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo to a residue

Sources & evidence

ORD record
ord-86ea114381174fdcb3273d5cd1ecc60c
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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