Methyl chloroformate → HCID 12085579, compound

HRID 1982817Notes

Reaction equation

HRID 1982817 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′-hydroxybenzophenone (0.87 g) in tetrahydrofuran (14 mL) was added triethylamine (0.53 mL) and methyl chloroformate (0.29 mL) at 0° C. After warming to room temperature, the mixture was stirred for 1.5 hours. 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. After warming to room temperature, and the mixture was stirred for 2.5 hours. To the reaction mixture was added 0.5 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and 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. customInsoluble 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. temperatureAfter warming to room temperature
  5. stirringthe mixture was stirred for 2.5 hours
  6. additionTo the reaction mixture was added 0.5 mol/L hydrochloric acid
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-8a9228210d0e4049b0a4b5c7b5e507ec
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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