Methyl chloroformate → HCID 11736683, compound

HRID 1950613Notes

Reaction equation

HRID 1950613 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=O.C(N(CC)CC)C.ClC(OC)=O>O1CCCC1>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:10][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[C:2]([OH:1])[CH:7]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 113228592-hydroxy-4-methoxy-3'-methoxy-benzophenone

Product 1

HCID 11736683HCID 11736683, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized by referring to Tetrahedron Lett., 1995, (30), 5335. To a solution of (2-hydroxy-4-methoxyphenyl)(3-methoxyphenyl)methanone (5.2 g) in tetrahydrofuran (100 ml) were sequentially added triethylamine (3.0 g) and methyl chloroformate (2.2 g) on an ice bath, the solution was stirred for 48 minutes, and then the reaction mixture was filtered. To a solution of sodium borohydride (3.0 g) in water (50 ml) was added dropwise the above-mentioned filtrate on an ice bath, and the solution was stirred for 1 hour and 10 minutes. The reaction solution was concentrated in vacuo, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (4.8 g).

Workup

  1. customThe title compound was synthesized
  2. filtrationthe reaction mixture was filtered
  3. additionTo a solution of sodium borohydride (3.0 g) in water (50 ml) was added dropwise the above-mentioned filtrate on an ice bath
  4. stirringthe solution was stirred for 1 hour and 10 minutes
  5. concentrationThe reaction solution was concentrated in vacuo
  6. extractionextracted with ethyl acetate
  7. washsequentially washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-238073b0e3d1461782439cdb670f0835
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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