Toluene → HCID 67958380, compound

HRID 527600Notes

Reaction equation

HRID 527600 reaction equation
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][O:16][CH3:17])[C:9]=1[C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:4])[CH3:3].[C:27]1(C)C=CC=CC=1>O.C(OCC)(=O)C>[CH2:22]([O:21][C:19](=[O:20])[C:18]([C:9]1[C:10]([O:14][CH2:15][O:16][CH3:17])=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][O:6][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:26])[CH3:25])=[CH2:27])[CH3:23]

Participants

5

Reactant 2

HCID 1140Toluene3×HCID 86698438HCID 86698438, compound2×

Product 1

HCID 67958380HCID 67958380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl (2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-{[(methyloxy)methyl]oxy}phenyl)(oxo)acetate (Intermediate 130, 1.4 g) in dry toluene (8 ml) dimethyl titanocene 9% w/w in toluene (Intermediate 131, 30 ml) was added and the reaction mixture was stirred for 1.5 hours at 90° C. After cooling the reaction was diluted with water (20 ml) and ethyl acetate (30 ml). Two phases were separated and the organic layer was dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a 100 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 9:1 as eluents. This afforded the title compound as a yellow pale oil (865 mg).

Workup

  1. temperatureAfter cooling the reaction
  2. customTwo phases were separated
  3. dry with materialthe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 100 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 9:1 as eluents

Sources & evidence

ORD record
ord-7d59cb5ac3d742dc8ee52a9b249ca4cb
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…