Triphenylcarbinol → HCID 15667221, compound

HRID 716073Notes

Reaction equation

HRID 716073 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[O:8][CH2:9][C@@H:10]([CH3:23])[O:11][CH2:12][P:13](=[O:22])([O:18][CH:19]([CH3:21])[CH3:20])[O:14][CH:15]([CH3:17])[CH3:16])C=CC=CC=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)O)C=CC=CC=1>C(O)(=O)C>[OH:8][CH2:9][C@@H:10]([CH3:23])[O:11][CH2:12][P:13](=[O:22])([O:14][CH:15]([CH3:17])[CH3:16])[O:18][CH:19]([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 6457TriphenylcarbinolHCID 53348326HCID 53348326, compound

Product 1

HCID 15667221HCID 15667221, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 90.6 g (0.182 mol) of diisopropyl (R)-[(2-triphenylmethoxy-1-methylethyloxy)methyl]phosphonate as a transparent yellow oil and 80% acetic acid solution (380 mL) were stirred to form a homogeneous solution, which was placed in 85° C. oil-bath and heated. The reaction was performed under stirring for 20 min, and then placed in an ice-bath for overnight to allow the side-product triphenylmethanol sufficiently to precipitate. After filtration, the filter cake was washed with 80% acetic acid solution (3×15 ml), and the filtrates were combined, and distilled at a reduced pressure to remove acetic acid and water. The residue was added to ethyl acetate (250 ml), and the mixture was washed with saturated brine (2×50 ml) to obtain an oil layer, which was dried over anhydrous sodium sulfate, and filtered. The filtrate was distilled at a reduced pressure to remove the solvent, and the residue was separated by a column chromatography (column chromatography conditions: silica gel 200-300 mesh; eluting agent was dichloromethane:methanol=50:1 to 10:1), to obtain diisopropyl (R)-[(2-hydroxy-1-methylethyloxy)methyl]phosphonate as a transparent light yellow oil product, 24.1 g.

Workup

  1. customto form a homogeneous solution, which
  2. customwas placed in 85° C.
  3. temperatureheated
  4. waitplaced in an ice-bath for overnight
  5. customto precipitate
  6. filtrationAfter filtration
  7. washthe filter cake was washed with 80% acetic acid solution (3×15 ml)
  8. distillationdistilled at a reduced pressure
  9. customto remove acetic acid and water
  10. additionThe residue was added to ethyl acetate (250 ml)
  11. washthe mixture was washed with saturated brine (2×50 ml)
  12. customto obtain an oil layer, which
  13. dry with materialwas dried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. distillationThe filtrate was distilled at a reduced pressure
  16. customto remove the solvent
  17. customthe residue was separated by a column chromatography (column chromatography conditions: silica gel 200-300 mesh; eluting agent was dichloromethane:methanol=50:1 to 10:1)

Sources & evidence

ORD record
ord-a30b86e2f56747748a6c1ce5bc017423
Source dataset
uspto-grants-2015_11
Patent number
US09187507B2

Reaction notes

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