Trityl chloride → (S)-Glycidyl Trityl Ether

HRID 1279764Notes

Reaction equation

HRID 1279764 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]1[O:23][C@H:22]1[CH2:24][OH:25].C(N(CC)CC)C>C(Cl)Cl>[C:2]1([C:1]([O:25][CH2:24][C@H:22]2[O:23][CH2:21]2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 6973630(-)-Glycidol

Product 1

HCID 7168113(S)-Glycidyl Trityl EtherYield 130.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trityl chloride (48.25 g, 173 mmol) in anhydrous CH2Cl2 (150 mL) was added to a stirred solution of (S)-(−)-glycidol (12.21 g, 164 mmol) and triethylamine (34.5 mL, 247 mmol) in anhydrous CH2Cl2 (250 mL) at −20° C. under a N2 atmosphere. After 2 h, CH2Cl2 was removed under vacuum. The mixture was taken up in EtOAc (500 mL) before it was washed with H2O (2×200 mL). The organic layer was dried, filtered and concentrated to give the crude title compound (67.9 g) contaminated with trityl alcohol, which can be removed by chromatography.

Workup

  1. customCH2Cl2 was removed under vacuum
  2. washwas washed with H2O (2×200 mL)
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-94ef27e361bd43e4beb172d5094a3702
Source dataset
uspto-grants-2002_09
Patent number
US06448422B1

Reaction notes

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