Methyl chloroformate → HCID 12085579, compound

HRID 1826627Notes

Reaction equation

HRID 1826627 reaction equation
[CH2:1]([O:4][C:5]1[CH:19]=[CH:18][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=O)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C(N(CC)CC)C.ClC(OC)=O>O1CCCC1>[CH2:1]([O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 12085578HCID 12085578, compound

Product 1

HCID 12085579HCID 12085579, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-allyloxy-2′-hydoxybenzophenone (0.87 g) in tetrahydrofuran (14 mL) were added triethylamine (0.53 mL) and methyl chloroformate (0.29 mL) at 0° C., and the mixture was stirred at room temperature for 1.5 hours. An insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. To a solution of the residue in tetrahydrofuran (18 mL) and water (9 mL) was added sodium borohydride (0.52 g) at 0° C., and the mixture was stirred at room temperature for 2.5 hours. To the reaction mixture was added 0.5 mol/L aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1) to give 2-(4-allyloxybenzyl)phenol (0.72 g).

Workup

  1. customAn insoluble material was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. additionTo a solution of the residue in tetrahydrofuran (18 mL) and water (9 mL) was added sodium borohydride (0.52 g) at 0° C.
  4. stirringthe mixture was stirred at room temperature for 2.5 hours
  5. additionTo the reaction mixture was added 0.5 mol/L aqueous hydrochloric acid solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-54f24d7e81b34db78d806824cf044569
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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